Herbicidal 3-substituted lactams

ABSTRACT

Also disclosed are compositions containing the compounds of Formula 1 and methods for controlling undesired vegetation comprising contacting the undesired vegetation or its environment with an effective amount of a compound or a composition of the invention.

FIELD OF THE INVENTION

This invention relates to certain herbicidal 3-substituted lactams,their N-oxides, salts and compositions, and methods of their use forcontrolling undesirable vegetation.

BACKGROUND OF THE INVENTION

The control of undesired vegetation is extremely important in achievinghigh crop efficiency. Achievement of selective control of the growth ofweeds especially in such useful crops as rice, soybean, sugar beet,maize, potato, wheat, barley, tomato and plantation crops, among others,is very desirable. Unchecked weed growth in such useful crops can causesignificant reduction in productivity and thereby result in increasedcosts to the consumer. The control of undesired vegetation in noncropareas is also important. Many products are commercially available forthese purposes, but the need continues for new compounds that are moreeffective, less costly, less toxic, environmentally safer or havedifferent sites of action. WO 2015/084796, WO 2016/003997 and WO2016/196593 disclose cyclic amides as herbicides. The compounds of thepresent invention are distinct from the compounds described in theseapplication publications. The herbicidal 3-substituted lactams of thepresent invention are not disclosed in these publications.

SUMMARY OF THE INVENTION

This disclosure relates, in part, to compounds of Formula 1 (includingall stereoisomers), N-oxides of such compounds, and salts of suchcompounds and N-oxides:

wherein

-   -   L is selected from

-   -   R^(A) is C₁-C₇ alkyl, C₁-C₇ haloalkyl, C₃-C₉ cycloalkyl, C₃-C₉        halocycloalkyl, C₁-C₇ alkoxy, C₁-C₇ haloalkoxy, C₃-C₉        cycloalkoxy, C₃-C₉ halocycloalkoxy, C₂-C₈ alkenyl, C₂-C₈        haloalkenyl, C₁-C₇ alkylamino, C₁-C₇ haloalkylamino, C₂-C₉        dialkylamino, C₂-C₉ halodialkylamino, C₃-C₉ cycloalkylamino or        C₃-C₉ halocycloalkylamino, each substituted or unsubstituted        with up to 3 substituents independently selected from R⁸ or G¹;        or    -   R^(A) is G¹ or OG¹; or    -   R^(A) is taken together with R⁹ as —C(R^(I))(R^(J))C(═O)— (i.e.        to form a ring);    -   R^(B) is H, C₁-C₄ alkoxy, C₁-C₄ haloalkyl or C₁-C₄ alkyl; or        phenyl substituted or unsubstituted with halogen or C₁-C₄ alkyl;    -   R^(C) is H, C₁-C₄ alkoxy, C₁-C₄ haloalkyl or C₁-C₄ alkyl; or        phenyl substituted or unsubstituted with halogen or C₁-C₄ alkyl;    -   R^(D) is H, C₁-C₄ alkyl or C₂-C₄ alkylcarbonyl;    -   R^(E) is H, hydroxy, amino, cyano, formyl, —C(O)NH₂, C₁-C₆        alkyl, C₁-C₆ haloalkyl, C₂-C₆ cyanoalkyl, C₃-C₆ cycloalkyl,        C₄-C₈ cycloalkylalkyl, C₂-C₈ alkoxyalkyl, C₃-C₈        alkoxyalkoxyalkyl, C₂-C₈ haloalkoxyalkyl, C₂-C₈ alkenyl, C₂-C₈        haloalkenyl, C₂-C₈ alkenylalkyl, C₂-C₈ haloalkenylalkyl, C₂-C₈        alkylcarbonyl, C₂-C₈ haloalkylcarbonyl, C₄-C₁₀        cycloalkylcarbonyl, C₅-C₁₀ cycloalkylcarbonylalkyl, C₂-C₈        alkoxycarbonyl, C₂-C₈ haloalkoxycarbonyl, C₄-C₁₀        cycloalkoxycarbonyl, C₂-C₈ alkylaminocarbonyl, C₃-C₁₀        dialkylaminocarbonyl, C₄-C₁₀ cycloalkylaminocarbonyl, C₁-C₆        alkoxy, C₁-C₆ alkylsulfinyl, C₁-C₆ haloalkylsulfinyl, C₃-C₈        cycloalkylsulfinyl, C₁-C₆ alkylsulfonyl, C₁-C₆        haloalkylsulfonyl, C₃-C₈ cycloalkylsulfonyl, C₁-C₆        alkylaminosulfonyl or C₂-C₈ dialkylaminosulfonyl; or G^(E) or        W^(E)G^(E);    -   R^(F) is H, formyl, —C(O)NH₂, C₂-C₈ alkylcarbonyl, C₂-C₈        haloalkylcarbonyl, C₄-C₁₀ cycloalkylcarbonyl, C₂-C₈        alkoxycarbonyl, C₂-C₈ haloalkoxycarbonyl, C₄-C₁₀        cycloalkoxycarbonyl, C₂-C₈ alkylaminocarbonyl, C₃-C₁₀        dialkylaminocarbonyl, C₄-C₁₀ cycloalkylaminocarbonyl, C₁-C₆        alkylsulfinyl, C₁-C₆ haloalkylsulfinyl, C₃-C₈        cycloalkylsulfinyl, C₁-C₆ alkylsulfonyl, C₁-C₆        haloalkylsulfonyl, C₃-C₈ cycloalkylsulfonyl, C₁-C₆        alkylaminosulfonyl, C₂-C₈ dialkylaminosulfonyl, —P(═O)(OH)₂,        C₁-C₆ dialkylphosphoryl, C₁-C₆ haloalkylphosphoryl, C₃-C₈        cycloalkylphosphoryl, C₂-C₈ dialkoxyphosphoryl, C₆-C₁₄        dicycloalkoxyphosphoryl, C₈-C₁₆ dicycloalkylalkoxyphosphoryl,        C₂-C₁₂ bis(alkylamino)phosphoryl, C₄-C₂₄        bis(dialkylamino)phosphoryl; or G^(F) or W^(F)G^(F);    -   R^(G) is formyl, —C(O)NH₂, C₂-C₈ alkylcarbonyl, C₂-C₈        haloalkylcarbonyl, C₄-C₁₀ cycloalkylcarbonyl, C₂-C₈        alkoxycarbonyl, C₂-C₈ haloalkoxycarbonyl, C₄-C₁₀        cycloalkoxycarbonyl, C₂-C₈ alkylaminocarbonyl, C₃-C₁₀        dialkylaminocarbonyl, C₄-C₁₀ cycloalkylaminocarbonyl, C₁-C₆        alkylsulfinyl, C₁-C₆ haloalkylsulfinyl, C₃-C₈        cycloalkylsulfinyl, C₁-C₆ alkylsulfonyl, C₁-C₆        haloalkylsulfonyl, C₃-C₈ cycloalkylsulfonyl, C₁-C₆        alkylaminosulfonyl, C₂-C₈ dialkylaminosulfonyl, —P(═O)(OH)₂,        C₁-C₆ dialkylphosphoryl, C₁-C₆ haloalkylphosphoryl, C₃-C₈        cycloalkylphosphoryl, C₂-C₈ dialkoxyphosphoryl, C₆-C₁₄        dicycloalkoxyphosphoryl, C₈-C₁₆ dicycloalkylalkoxyphosphoryl,        C₂-C₁₂ bis(alkylamino)phosphoryl, C₄-C₂₄        bis(dialkylamino)phosphoryl; or phenyl substituted or        unsubstituted with R¹⁶; or W^(G)G^(G);    -   R^(I) is H, C₁-C₄ alkoxy, C₁-C₄ haloalkyl or C₁-C₄ alkyl; or        phenyl substituted or unsubstituted with halogen or C₁-C₄ alkyl;    -   R^(J) is H, C₁-C₄ alkoxy, C₁-C₄ haloalkyl or C₁-C₄ alkyl; or        phenyl substituted or unsubstituted with halogen or C₁-C₄ alkyl;    -   Q¹ is a phenyl ring or a naphthalenyl ring system, each ring or        ring system substituted or unsubstituted with up to 5        substituents independently selected from R⁷; or a 4- to        7-membered heterocyclic ring; or an 8- to 10-membered bicyclic        ring system, each ring or ring system containing ring members        selected from carbon atoms and 1 to 5 heteroatoms independently        selected from up to 2 O, up to 2 S and up to 5 N atoms, wherein        up to 3 carbon ring members are independently selected from        C(═O) and C(═S), and the sulfur atom ring members are        independently selected from S(═O)_(u)(═NR¹⁴)_(v), each ring or        ring system substituted or unsubstituted with up to 5        substituents independently selected from R¹⁰ on carbon atom ring        members and selected from R¹² on nitrogen atom ring members; or    -   Q² is a phenyl ring or a naphthalenyl ring system, each ring or        ring system substituted or unsubstituted with up to 5        substituents independently selected from R¹⁰; or a 4- to        7-membered heterocyclic ring; or an 8- to 10-membered bicyclic        ring system, each ring or ring system containing ring members        selected from carbon atoms and 1 to 4 heteroatoms independently        selected from up to 2 O, up to 2 S and up to 5 N atoms, wherein        up to 3 carbon ring members are independently selected from        C(═O) and C(═S), and the sulfur atom ring members are        independently selected from S(═O)_(u)(═NR¹⁴)_(v), each ring or        ring system substituted or unsubstituted with up to 5        substituents independently selected from R¹¹ on carbon atom ring        members and selected from R¹³ on nitrogen atom ring members; or    -   J is —CR²R³—, —CR²R³—CR⁴R⁵—, —NR⁶— or —O—;    -   Y¹ and Y² are each independently O, S or NR¹⁵;    -   R¹ is H, hydroxy, amino, cyano, formyl, C₃-C₈        alkylcarbonylalkyl, —C(C₁-C₄ alkyl)=N—O(C₁-C₄ alkyl), —C(O)NH₂,        C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₂-C₆ alkenyl, C₃-C₆ alkynyl,        C₂-C₆ cyanoalkyl, C₃-C₆ cycloalkyl, C₃-C₈ cycloalkenyl, C₄-C₈        cycloalkylalkyl, C₂-C₈ alkoxyalkyl, C₃-C₈ alkoxyalkoxyalkyl,        C₂-C₈ haloalkoxyalkyl, C₂-C₈ haloalkenylalkyl, C₂-C₈        alkylthioalkyl, C₂-C₈ alkylsulfinylalkyl, C₂-C₈        alkylsulfonylalkyl, C₂-C₈ alkylcarbonyl, C₂-C₈        haloalkylcarbonyl, C₄-C₁₀ cycloalkylcarbonyl, C₅-C₁₀        cycloalkylcarbonylalkyl, C₂-C₈ alkoxycarbonyl, C₂-C₈        haloalkoxycarbonyl, C₄-C₁₀ cycloalkoxycarbonyl, C₂-C₈        alkylaminocarbonyl, C₃-C₁₀ dialkylaminocarbonyl, C₄-C₁₀        cycloalkylaminocarbonyl, C₁-C₆ alkoxy, C₁-C₆ alkylthio, C₁-C₆        haloalkylthio, C₃-C₈ cycloalkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆        haloalkylsulfinyl, C₃-C₈ cycloalkylsulfinyl, C₁-C₆        alkylsulfonyl, C₁-C₆ haloalkylsulfonyl, C₃-C₈        cycloalkylsulfonyl, C₁-C₆ alkylaminosulfonyl, C₂-C₈        dialkylaminosulfonyl, C₃-C₁₀ trialkylsilyl; or —CPh=N—O(C₁-C₄        alkyl), each substituted or unsubstituted on ring members with        up to 5 substituents independently selected from R¹³; or G¹;    -   R² and R³ are each independently H, halogen, hydroxy, C₁-C₄        alkyl, C₁-C₄ haloalkyl or C₁-C₄ alkoxy; or    -   R² and R³ are taken together with the carbon atom to which they        are bonded to form a C₃-C₇ cycloalkyl ring;    -   R⁴ and R⁵ are each independently H, halogen, hydroxy, C₁-C₄        alkyl, C₁-C₄ haloalkyl or C₁-C₄ alkoxy;    -   R⁶ is C₁-C₆ alkyl, C₂-C₆ alkenyl, C₃-C₆ alkynyl or C₁-C₆ alkoxy;        or    -   R¹ and R⁶ are taken together as C₃-C₆ alkylene or —CH₂OCH₂—;    -   R⁷ is H, halogen, hydroxy, C₁-C₄ alkoxy, C₁-C₄ haloalkyl or        C₁-C₄ alkyl;    -   each R⁸ is independently cyano, hydroxy, amino, nitro, —CHO,        —C(═O)OH, —C(═O)NH₂, —SO₂NH₂, C₂-C₆ alkenyl, C₂-C₆ alkynyl,        C₂-C₈ alkylcarbonyl, C₂-C₈ haloalkylcarbonyl, C₂-C₈        alkoxycarbonyl, C₄-C₁₀ cycloalkoxycarbonyl, C₅-C₁₂        cycloalkylalkoxycarbonyl, C₂-C₈ alkylaminocarbonyl, C₃-C₁₀        dialkylaminocarbonyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, C₂-C₈        alkylcarbonyloxy, C₁-C₆ alkylthio, C₁-C₆ haloalkylthio, C₁-C₆        alkylsulfinyl, C₁-C₆ haloalkylsulfinyl, C₁-C₆ alkylsulfonyl,        C₁-C₆ haloalkylsulfonyl, C₁-C₆ alkylaminosulfonyl, C₂-C₈        dialkylaminosulfonyl, C₃-C₁₀ trialkylsilyl, C₁-C₆ alkylamino,        C₂-C₈ dialkylamino, C₂-C₈ alkylcarbonylamino or C₁-C₆        alkylsulfonylamino;    -   R⁹ is H, hydroxy, amino, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₂-C₆        alkenyl, C₃-C₆ alkynyl, C₂-C₈ alkoxyalkyl, C₂-C₈        haloalkoxyalkyl, C₂-C₈ alkylthioalkyl, C₂-C₈ alkylsulfinylalkyl,        C₂-C₈ alkylsulfonylalkyl, C₂-C₈ alkylcarbonyl, C₂-C₈        haloalkylcarbonyl, C₄-C₁₀ cycloalkylcarbonyl, C₂-C₈        alkoxycarbonyl, C₂-C₈ haloalkoxycarbonyl, C₄-C₁₀        cycloalkoxycarbonyl, C₂-C₈ alkylaminocarbonyl, C₃-C₁₀        dialkylaminocarbonyl, C₄-C₁₀ cycloalkylaminocarbonyl, C₁-C₆        alkoxy, C₁-C₆ alkylthio, C₁-C₆ haloalkylthio, C₃-C₈        cycloalkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆ haloalkylsulfinyl,        C₃-C₈ cycloalkylsulfinyl, C₁-C₆ alkylsulfonyl, C₁-C₆        haloalkylsulfonyl, C₃-C₈ cycloalkylsulfonyl, C₁-C₆        alkylaminosulfonyl, C₂-C₈ dialkylaminosulfonyl or C₃-C₁₀        trialkylsilyl or G¹;    -   each R¹⁰ and R¹¹ is independently halogen, hydroxy, cyano,        nitro, amino, C₁-C₈ alkyl, C₁-C₈ cyanoalkyl, C₁-C₈ cyanoalkoxy,        C₁-C₈ haloalkyl, C₁-C₈ hydroxyalkyl, C₁-C₈ nitroalkyl, C₂-C₈        alkenyl, C₂-C₈ haloalkenyl, C₂-C₈ nitroalkenyl, C₂-C₈ alkynyl,        C₂-C₈ haloalkynyl, C₂-C₈ alkoxyalkyl, C₃-C₈ alkoxyalkoxyalkyl,        C₂-C₈ haloalkoxyalkyl, C₂-C₈ haloalkoxyhaloalkoxy, C₃-C₆        cycloalkyl, cyclopropylmethyl, 1-methylcyclopropyl,        2-methylcyclopropyl, C₄-C₁₀ cycloalkylalkyl, C₄-C₁₀        halocycloalkylalkyl, C₅-C₁₂ alkylcycloalkylalkyl, C₅-C₁₂        cycloalkylalkenyl, C₅-C₁₂ cycloalkylalkynyl, C₃-C₈ cycloalkyl,        C₃-C₈ halocycloalkyl, C₄-C₁₀ alkylcycloalkyl, C₆-C₁₂        cycloalkylcycloalkyl, C₃-C₈ cycloalkenyl, C₃-C₈        halocycloalkenyl, C₂-C₈ haloalkoxyalkoxy, C₂-C₈ alkoxyalkoxy,        C₄-C₁₀ cycloalkoxyalkyl, C₂-C₈ alkylthioalkyl, C₂-C₈        alkylsulfinylalkyl, C₂-C₈ alkylsulfonylalkyl, C₂-C₈ alkylamino,        C₂-C₈ dialkylamino, C₂-C₈ halodialkylamino, C₂-C₈        alkylaminoalkyl, C₂-C₈ haloalkylaminoalkyl, C₄-C₁₀        cycloalkylaminoalkyl, C₃-C₁₀ dialkylaminoalkyl, —CHO, C₂-C₈        alkylcarbonyl, C₂-C₈ haloalkylcarbonyl, C₄-C₁₀        cycloalkylcarbonyl, —C(═O)OH, C₂-C₈ alkoxycarbonyl, C₂-C₈        haloalkoxycarbonyl, C₄-C₁₀ cycloalkoxycarbonyl, C₅-C₁₂        cycloalkylalkoxycarbonyl, —C(═O)NH₂, C₂-C₈ alkylaminocarbonyl,        C₄-C₁₀ cycloalkylaminocarbonyl, C₃-C₁₀ dialkylaminocarbonyl,        C₁-C₈ alkoxy, C₁-C₈ haloalkoxy, C₂-C₈ alkenyloxy, C₂-C₈        haloalkenyloxy, C₃-C₈ alkynyloxy, C₃-C₈ haloalkynyloxy, C₃-C₈        cycloalkoxy, C₃-C₈ halocycloalkoxy, C₄-C₁₀ cycloalkylalkoxy,        C₃-C₁₀ alkylcarbonylalkoxy, C₂-C₈ alkylcarbonyloxy, C₂-C₈        haloalkylcarbonyloxy, C₄-C₁₀ cycloalkylcarbonyloxy, C₁-C₈        alkylsulfonyloxy, C₁-C₈ haloalkylsulfonyloxy, C₁-C₈ alkylthio,        C₁-C₈ haloalkylthio, C₃-C₈ cycloalkylthio, C₁-C₈ alkylsulfinyl,        C₁-C₈ haloalkylsulfinyl, C₁-C₈ alkylsulfonyl, C₁-C₈        haloalkylsulfonyl, C₃-C₈ cycloalkylsulfonyl, formylamino, C₂-C₈        alkylcarbonylamino, C₂-C₈ haloalkylcarbonylamino, C₃-C₈        cycloalkylamino, C₂-C₈ alkoxycarbonylamino, C₁-C₆        alkylsulfonylamino, C₁-C₆ haloalkylsulfonylamino, —SF₅, —SCN,        SO₂NH₂, C₃-C₁₂ trialkylsilyl, C₄-C₁₂ trialkylsilylalkyl or        C₄-C₁₂ trialkylsilylalkoxy; or G²; or R²⁰S(═O)═N—,        R²⁰S(═O)₂NR¹⁹—C(═O)— or R²⁰(R¹⁹N═)_(q)S(═O)_(p)—, wherein the        free bond projecting to the right indicates the connecting point        to Q¹; or    -   each R¹² and R¹³ is independently cyano, C₁-C₃ alkyl, C₁-C₈        hydroxyalkyl, C₂-C₃ alkenyl, C₂-C₃ alkynyl, C₃-C₆ cycloalkyl,        C₂-C₃ alkoxyalkyl, C₁-C₃ alkoxy, C₂-C₃ alkylcarbonyl, C₂-C₃        alkoxycarbonyl, C₂-C₃ alkylaminoalkyl or C₃-C₄        dialkylaminoalkyl;    -   each R¹⁴ is independently H, cyano, C₂-C₃ alkylcarbonyl or C₂-C₃        haloalkylcarbonyl;    -   each R¹⁵ is independently H, cyano, hydroxy, CHO, C₁-C₄ alkyl,        C₁-C₄ haloalkyl, C₁-C₄ alkoxy, C₂-C₆ alkylcarbonyl, C₂-C₆        haloalkylcarbonyl, —(C═O)CH₃ or —(C═O)CF₃;    -   each G¹ is independently phenyl; or a 5- or 6-membered        heterocyclic ring, each substituted or unsubstituted on ring        members with up to 5 substituents independently selected from        R¹⁷;    -   each W^(E), W^(F) and W^(G) is independently —C(═O)—, —C(═O)O—,        —C(═O)NH— or —S(═O)₂—;    -   each G^(E), G^(F) and G^(G) is independently phenyl substituted        or unsubstituted with R¹⁶; or a 5- or 6-membered heterocyclic        ring, each heterocyclic ring substituted or unsubstituted on        ring members with up to 5 substituents independently selected        from R¹⁶;    -   each G² is independently phenyl, phenylmethyl (i.e. benzyl),        pyridinylmethyl, phenylcarbonyl (i.e. benzoyl), phenoxy,        phenylethynyl, phenylsulfonyl or a 5- or 6-membered heterocyclic        ring, each substituted or unsubstituted on ring members with up        to 5 substituents independently selected from R¹⁸;    -   each R¹⁶, R¹⁷ and R¹⁸ is independently halogen, cyano, hydroxy,        amino, nitro, —CHO, —C(═O)OH, —C(═O)NH₂, —SO₂NH₂, C₁-C₆ alkyl,        C₁-C₆ haloalkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₂-C₈        alkylcarbonyl, C₂-C₈ haloalkylcarbonyl, C₂-C₈ alkoxycarbonyl,        C₄-C₁₀ cycloalkoxycarbonyl, C₅-C₁₂ cycloalkylalkoxycarbonyl,        C₂-C₈ alkylaminocarbonyl, C₃-C₁₀ dialkylaminocarbonyl, C₁-C₆        alkoxy, C₁-C₆ haloalkoxy, C₂-C₈ alkylcarbonyloxy, C₁-C₆        alkylthio, C₁-C₆ haloalkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆        haloalkylsulfinyl, C₁-C₆ alkylsulfonyl, C₁-C₆ haloalkylsulfonyl,        C₁-C₆ alkylaminosulfonyl, C₂-C₈ dialkylaminosulfonyl, C₃-C₁₀        trialkylsilyl, C₁-C₆ alkylamino, C₂-C₈ dialkylamino, C₂-C₈        alkylcarbonylamino, C₁-C₆ alkylsulfonylamino, phenyl, pyridinyl        or thienyl;    -   each R¹⁹ is independently H, cyano, C₂-C₃ alkylcarbonyl or C₂-C₃        haloalkylcarbonyl;    -   each R²⁰ is independently H, C₁-C₆ alkyl, C₃-C₈ cycloalkyl,        C₄-C₈ cycloalkylalkyl, C₁-C₆ haloalkyl, C₂-C₆ alkenyl, C₃-C₆        alkynyl, C₂-C₈ alkoxyalkyl, C₂-C₈ haloalkoxyalkyl, C₂-C₈        alkylthioalkyl, C₂-C₈ alkylsulfinylalkyl, C₂-C₈        alkylsulfonylalkyl, C₁-C₆ alkoxy or C₃-C₁₀ trialkylsilyl; or G¹;    -   each u and v are independently 0, 1 or 2 in each instance of        S(═O)_(u)(═NR¹⁴)_(v), provided that the sum of u and v is 0, 1        or 2; and    -   each p and q are independently 0, 1 or 2 in each instance of        R²⁰(R¹⁹N═)_(q)S(═O)_(p)—, provided that the sum of u and v is 0,        1 or 2 and when p is 0, q is other than 1 or 2.

More particularly, this invention pertains to a compound of Formula 1(including all stereoisomers), an N-oxide or a salt thereof. Thisinvention also relates to a herbicidal composition comprising a compoundof the invention (i.e. in a herbicidally effective amount) and at leastone component selected from the group consisting of surfactants, soliddiluents and liquid diluents. This invention further relates to a methodfor controlling the growth of undesired vegetation comprising contactingthe vegetation or its environment with a herbicidally effective amountof a compound of the invention (e.g., as a composition describedherein).

This invention also includes a herbicidal mixture comprising (a) acompound selected from Formula 1, N-oxides, and salts thereof, and (b)at least one additional active ingredient selected from (b1) through(b16); and salts of compounds of (b1) through (b16), as described below.

DETAILS OF THE INVENTION

As used herein, the terms “comprises,” “comprising,” “includes,”“including,” “has,” “having,” “contains”, “containing,” “characterizedby” or any other variation thereof, are intended to cover anon-exclusive inclusion, subject to any limitation explicitly indicated.For example, a composition, mixture, process or method that comprises alist of elements is not necessarily limited to only those elements butmay include other elements not expressly listed or inherent to suchcomposition, mixture, process or method.

The transitional phrase “consisting of” excludes any element, step, oringredient not specified. If in the claim, such would close the claim tothe inclusion of materials other than those recited except forimpurities ordinarily associated therewith. When the phrase “consistingof” appears in a clause of the body of a claim, rather than immediatelyfollowing the preamble, it limits only the element set forth in thatclause; other elements are not excluded from the claim as a whole.

The transitional phrase “consisting essentially of” is used to define acomposition or method that includes materials, steps, features,components, or elements, in addition to those literally disclosed,provided that these additional materials, steps, features, components,or elements do not materially affect the basic and novelcharacteristic(s) of the claimed invention. The term “consistingessentially of” occupies a middle ground between “comprising” and“consisting of”.

Where applicants have defined an invention or a portion thereof with anopen-ended term such as “comprising,” it should be readily understoodthat (unless otherwise stated) the description should be interpreted toalso describe such an invention using the terms “consisting essentiallyof” or “consisting of.”

Further, unless expressly stated to the contrary, “or” refers to aninclusive or and not to an exclusive or. For example, a condition A or Bis satisfied by any one of the following: A is true (or present) and Bis false (or not present), A is false (or not present) and B is true (orpresent), and both A and B are true (or present).

Also, the indefinite articles “a” and “an” preceding an element orcomponent of the invention are intended to be nonrestrictive regardingthe number of instances (i.e. occurrences) of the element or component.Therefore “a” or “an” should be read to include one or at least one, andthe singular word form of the element or component also includes theplural unless the number is obviously meant to be singular.

As referred to herein, the term “seedling”, used either alone or in acombination of words means a young plant developing from the embryo of aseed.

As referred to herein, the term “broadleaf” used either alone or inwords such as “broadleaf weed” means dicot or dicotyledon, a term usedto describe a group of angiosperms characterized by embryos having twocotyledons.

As used herein, the term “alkylating agent” refers to a chemicalcompound in which a carbon-containing radical is bound through a carbonatom to a leaving group such as halide or sulfonate, which isdisplaceable by bonding of a nucleophile to said carbon atom. Unlessotherwise indicated, the term “alkylating” does not limit thecarbon-containing radical to alkyl.

In the above recitations, the term “alkyl”, used either alone or incompound words such as “alkylthio” or “haloalkyl” includesstraight-chain or branched alkyl, such as, methyl, ethyl, n-propyl,i-propyl, or the different butyl, pentyl or hexyl isomers. “Alkenyl”includes straight-chain or branched alkenes such as ethenyl, 1-propenyl,2-propenyl, and the different butenyl, pentenyl and hexenyl isomers.“Alkenyl” also includes polyenes such as 1,2-propadienyl and2,4-hexadienyl. “Alkynyl” includes straight-chain or branched alkynessuch as ethynyl, 1-propynyl, 2-propynyl and the different butynyl,pentynyl and hexynyl isomers. “Alkynyl” can also include moietiescomprised of multiple triple bonds such as 2,5-hexadiynyl. “Alkylene”denotes a straight-chain or branched alkanediyl. Examples of “alkylene”include CH₂CH₂CH₂, CH₂CH(CH₃) and the different butylene, pentylene andhexylene isomers.

“Alkoxy” includes, for example, methoxy, ethoxy, n-propyloxy,isopropyloxy and the different butoxy, pentoxy and hexyloxy isomers.“Alkoxyalkyl” denotes alkoxy substitution on alkyl. Examples of“alkoxyalkyl” include CH₃OCH₂, CH₃OCH₂CH₂, CH₃CH₂OCH₂, CH₃CH₂CH₂CH₂OCH₂and CH₃CH₂OCH₂CH₂. “Alkoxyalkoxyalkyl” denotes at least alkoxysubstitution on the alkoxy moiety of alkoxyalkyl moiety. Examples of“alkoxyalkoxyalkyl” include CH₃OCH₂OCH₂—, CH₃CH₂O(CH₃)CHOCH₂— and(CH₃O)₂CHOCH₂—. “Alkoxyalkoxy” denotes alkoxy substitution on alkoxy.Examples of alkoxyalkoxy include CH₃CH₂OCH₂O, (CH₃)₂CHOCH₂CH₂O andCH₃CH₂CH₂OCH₂O. “Alkenyloxy” includes straight-chain or branchedalkenyloxy moieties. Examples of “alkenyloxy” include H₂C═CHCH₂O,(CH₃)₂C═CHCH₂O, (CH₃)CH═CHCH₂O, (CH₃)CH═C(CH₃)CH₂O and CH₂═CHCH₂CH₂O.“Alkynyloxy” includes straight-chain or branched alkynyloxy moieties.Examples of “alkynyloxy” include HC≡CCH₂O, CH₃C≡CCH₂O and CH₃C≡CCH₂CH₂O.“Alkylthio” includes branched or straight-chain alkylthio moieties suchas methylthio, ethylthio, and the different propylthio, butylthio,pentylthio and hexylthio isomers. “Alkylsulfinyl” includes bothenantiomers of an alkylsulfinyl group. Examples of “alkylsulfinyl”include CH₃S(O)—, CH₃CH₂S(O)—, CH₃CH₂CH₂S(O)—, (CH₃)₂CHS(O)— and thedifferent butylsulfinyl, pentylsulfinyl and hexylsulfinyl isomers.“Alkylsulfonyl” indicates a sulfonyl moiety substituted with astraight-chain or branched alkyl group. Examples of “alkylsulfonyl”include CH₃S(O)₂—, CH₃CH₂S(O)₂—, CH₃CH₂CH₂S(O)₂—, (CH₃)₂CHS(O)₂—, andthe different butylsulfonyl, pentylsulfonyl and hexylsulfonyl isomers.“Alkylthioalkyl” denotes alkylthio substitution on alkyl. Examples of“alkylthioalkyl” include CH₃SCH₂, CH₃SCH₂CH₂, CH₃CH₂SCH₂,CH₃CH₂CH₂CH₂SCH₂ and CH₃CH₂SCH₂CH₂. “Alkylsulfinylalkyl” denotesalkylsulfinyl substitution on alkyl. Examples of “alkylsulfinylalkyl”include CH₃S(═O)CH₂, CH₃S(═O)CH₂CH₂, CH₃CH₂S(═O)CH₂ andCH₃CH₂S(═O)CH₂CH₂. “Alkylsulfonylalkyl” denotes alkylsulfonylsubstitution on alkyl. Examples of “alkylsulfonylalkyl” includeCH₃S(═O)₂CH₂, CH₃S(═O)₂CH₂CH₂, CH₃CH₂S(═O)₂CH₂ and CH₃CH₂S(═O)₂CH₂CH₂.Examples of “alkylsulfonyloxy” include CH₃S(O)₂O—, CH₃CH₂S(O)₂O— andCH₃CH₂CH₂S(O)₂O—. “Alkylamino”, “dialkylamino”, “halodialkylamino” andthe like, are defined analogously to the above examples. Examples of“alkylsulfonylamino” include CH₃S(═O)NH— and CH₂CH₂CH₂S(═O)NH—. Examplesof “alkylaminoalkyl” include CH₃NHCH₂—, (CH₃)₂CHNHCH₂— andCH₃NHCH(CH₃)—. Examples of “dialkylaminoalkyl” include (CH₃)₂NCH₂—,(CH₃)₂NC(CH₃)H— and (CH₃)(CH₃)NCH₂—. Examples of “alkylaminocarbonyl”include (CH₃)NHC(O)— and (CH₃CH₂)NHC(O)—. An example of“dialkylaminocarbonyl” is (CH₃)₂NC(O)—. An example of“alkylaminosulfonyl” is (CH₃)NHS(O)₂— and an example of“dialkylaminosulfonyl” is (CH₃)₂NS(O)₂—. The term “alkylcarbonylamino”denotes a straight-chain or branched alkyl moiety bonded to the C(═O)moiety of carbonylamino group. Examples of “alkylcarbonylamino” includeCH₃C(═O)NH— and CH₃CH₂C(═O)NH—. The term “alkoxycarbonylamino” denotes astraight-chain or branched alkoxy moiety bonded to the C(═O) moiety ofcarbonylamino group. Examples of “alkoxycarbonylamino” includeCH₃OC(═O)NH— and CH₃CH₂OC(═O)NH—.

“Cycloalkyl” includes, for example, cyclopropyl, cyclobutyl, cyclopentyland cyclohexyl. The term “alkylcycloalkyl” denotes alkyl substitution ona cycloalkyl moiety and includes, for example, ethylcyclopropyl,i-propylcyclobutyl, 3-methylcyclopentyl and 4-methylcyclohexyl. The term“cycloalkylalkyl” denotes cycloalkyl substitution on an alkyl moiety.Examples of “cycloalkylalkyl” include cyclopropylmethyl,cyclopentylethyl, and other cycloalkyl moieties bonded to straight-chainor branched alkyl groups. Examples of the term “alkylcycloalkylalkyl”include 1-methylcyclopropylmethyl and 2-methylcyclopentylethyl. The term“cycloalkylalkenyl” denotes cycloalkyl bonded to an alkenyl moiety. Theterm “cycloalkylcycloalkyl” denotes cycloalkyl substitution on acycloalkyl moiety by a single bond. The term “cycloalkylalkynyl” denotescycloalkyl bonded to an alkynyl moiety. The term “cycloalkylamino”denotes cycloalkyl bonded to an amino moiety. The term“cycloalkylaminocarbonyl” denotes cycloalkyl bonded to an aminocarbonylmoiety. The term “cycloalkylaminoalkyl” denotes cycloalkyl bonded to anaminoalkyl moiety. The term “cycloalkylcarbonyl” denotes cycloalkylbonded to a carbonyl moiety. The term “cycloalkylcarbonylalkyl” denotescycloalkyl bonded to a carbonylalkyl moiety. The term“cycloalkylcarbonyloxy” denotes cycloalkyl bonded to the carbon atom ofa carbonyloxy moiety. The term “cycloalkoxy” denotes cycloalkyl linkedthrough an oxygen atom such as cyclopentyloxy and cyclohexyloxy. Theterm “cycloalkoxyalkyl” denotes cycloalkoxy linked through an alkylmoiety. The terms “cycloalkylthio”, “cycloalkylsulfinyl” and“cycloalkylsulfonyl” denotes cycloalkyl bonded through a sulfur,sulfinyl or sulfonyl moiety, respectively.

The term “cycloalkoxycarbonyl” denotes cycloalkoxy linked through acarbonyl moiety. “Cycloalkylalkoxy” denotes cycloalkylalkyl linkedthrough an oxygen atom attached to the alkyl chain. Examples of“cycloalkylalkoxy” include cyclopropylmethoxy, cyclopentylethoxy, andother cycloalkyl moieties bonded to straight-chain or branched alkoxygroups. “Cycloalkenyl” includes groups such as cyclopentenyl andcyclohexenyl as well as groups with more than one double bond such as1,3- and 1,4-cyclohexadienyl. The term “halocycloalkenyl” denoteshalogen substitution on the cycloalkenyl moiety.

The term “halogen”, either alone or in compound words such as“haloalkyl”, or when used in descriptions such as “alkyl substitutedwith halogen” includes fluorine, chlorine, bromine or iodine. Further,when used in compound words such as “haloalkyl”, or when used indescriptions such as “alkyl substituted with halogen” said alkyl may bepartially or fully substituted with halogen atoms which may be the sameor different. Examples of “haloalkyl” or “alkyl substituted withhalogen” include F₃C, ClCH₂, CF₃CH₂ and CF₃CCl₂. The terms“halocycloalkyl”, “halocycloalkylalkyl”, “halocycloalkoxy”,“haloalkoxy”, “haloalkoxyalkoxy”, “haloalkylthio”, “haloalkylsulfinyl”,“haloalkylsulfonyl”, “haloalkenyl”, “haloalkynyl”, “haloalkenyloxy”,“haloalkenylalkyl”, “haloalkylcarbonyl”, “haloalkylcarbonylamino”,“haloalkylsulfonylamino”, “haloalkoxyhaloalkoxy”,“haloalkylsulfonyloxy”, “haloalkynyloxy”, “haloalkoxyalkyl”,“haloalkylcarbonyloxy”, “haloalkylaminoalkyl” and the like, are definedanalogously to the term “haloalkyl”. Examples of “haloalkoxy” includeCF₃O—, CCl₃CH₂O—, HCF₂CH₂CH₂O— and CF₃CH₂O—. Examples of “haloalkylthio”include CCl₃S—, CF₃S—, CCl₃CH₂S— and ClCH₂CH₂CH₂S—. Examples of“haloalkylsulfinyl” include CF₃S(O)—, CCl₃S(O)—, CF₃CH₂S(O)— andCF₃CF₂S(O)—. Examples of “haloalkylsulfonyl” include CF₃S(O)₂—,CCl₃S(O)₂—, CF₃CH₂S(O)₂— and CF₃CF₂S(O)₂—. Examples of“haloalkylsulfonyloxy” include CHCl₂S(O)₂O—, CH₂ClCH₂S(O)₂O— andCH₃CHClCH₂S(O)₂O—. Examples of “haloalkenyl” include (Cl)₂C═CHCH₂— andCF₃CH₂CH═CHCH₂—. Examples of “haloalkenyloxy” include (Cl)₂C═CHCH₂O— andCF₃CH₂CH═CHCH₂O—. Examples of “haloalkynyl” include HC≡CCHCl—, CF₃C≡C—,CCl₃C≡C— and FCH₂C≡CCH₂—. Examples of “haloalkynyloxy” includeHC≡CCHClO—, CCl₃C≡C— and FCH₂C≡CCH₂O—. Examples of “haloalkoxyalkyl”include CF₃OCH₂—, ClCH₂CH₂OCH₂CH₂—, Cl₃CCH₂OCH₂— as well as branchedalkyl derivatives. Examples of “haloalkoxycarbonyl” include CF₃OC(O)—,ClCH₂CH₂OCH₂CH₂—, Cl₃CCH₂OCH₂OC(O)— as well as branched alkylderivatives.

“Alkylcarbonyl” denotes a straight-chain or branched alkyl moiety bondedto a C(═O) moiety. “Alkoxycarbonyl” denotes a straight-chain or branchedalkoxy moiety bonded to a C(═O) moiety. Examples of “alkylcarbonyl”include CH₃C(═O)—, CH₃CH₂CH₂C(═O)— and (CH₃)₂CHC(═O)—. Examples of“alkoxycarbonyl” include CH₃OC(═O)—, CH₃CH₂OC(═O)—, CH₃CH₂CH₂OC(═O)—,(CH₃)₂CHOC(═O)— and the different butoxy- or pentoxycarbonyl isomers.“Cycloalkylalkoxycarbonyl” denotes a cycloalkylalkyl moieties bonded toan oxygen atom of alkoxycarbonyl moiety. Examples of“cycloalkylalkoxycarbonyl” include cyclopropyl-CH₂OC(═O)—,cyclopropyl-CH(CH₃)OC(═O)— and cyclopentyl-CH₂OC(═O)—.“Alkylcarbonylalkyl” denotes a straight-chain or branched chain alkylgroup bonded to the carbon atom of to a carbonylalkyl moiety. Examplesof “alkylcarbonylalkyl” include (CH₃)C(═O)CH₂— and (CH₃CH₂)C(═O)CH₂—.“Alkylcarbonyloxy” denotes a straight-chain or branched-chain alkylgroup bonded to the carbon atom of to a carbonyloxy moiety. Examples of“alkylcarbonyloxy” include (CH₃)C(═O)O— and (CH₃CH₂)C(═O)O—.

The term “dialkylphosphoryl” refers to a phosine oxide derivative.Examples of “dialkylphosphoryl” include —P(═O)(CH₃)₂ and—P(═O)(CH₂CH₃)₂. The term “haloalkylphosphoryl” refers to a halogenatedphosphine oxide derivative. Examples of “haloalkylphosphory” includeP(═O)(CH₂Cl)₂ and —P(═O)(CH₂CH₂Br)₂ and —P(═O)(CH₂CH₂CH₂CF₂)₂. The term“cycloalkylphosphoryl” refers to a cycloalkyl phosphine oxidederivative. Examples of “cycloalkylphosphoryl” include —P(═O)(c-Pr)₂ and—P(═O)(c-hex)₂. The term “dialkoxyphosphoryl” refers to a phosphonicacid derivative. Examples of “dialkoxyphosphoryl” include —P(═O)(OCH₃)₂and —P(═O)(OCH₂CH₃)₂. The term “dicycloalkylalkoxyphosphoryl” refers toa phosphonic acid derivative. Examples of “dicycloalkylalkoxyphophoryl”include —P(═O)(O-c-Pr)₂ and —P(═O)(O-c-Bu)₂. Examples ofbis(alkylamino)phosphoryl include —P(═O)(NHCH₃)₂ and —P(═O)(NHCH₂CH₃)₂.Examples of bis(dialkylamino)phosphoryl include —P(═O)(N(CH₃)₂)₂, and—P(═O)(N(CH₂CH₂CH₃)₂)₂.

The term “cyanoalkyl” or “cyanoalkoxy” means a cyano group bondedthrough an alkyl or alkoxy moiety, respectively. The carbon in the cyanogroup is not included in the total number of carbon atoms for this term.The term “nitroalkyl” or “nitroalkenyl” represents a nitro group bondedthrough an alkyl or alkenyl moiety, respectively. The term“hydroxyalkyl” means a hydroxyl group bonded through an alkyl moiety.The term “trialkylsilyl” means three alkyl groups bonded throughsilicon. The term “trialkylsilylalkyl” means three alkyl groups bondedthrough a silylalkyl moiety. The term “trialkylsilylalkoxy” means threealkyl groups bonded through a silylalkoxy moiety.

The total number of carbon atoms in a substituent group is indicated bythe “C_(i)-C_(j)” prefix where i and j are numbers from 1 to 24. Forexample, C₁-C₄ alkylsulfonyl designates methylsulfonyl throughbutylsulfonyl; C₂ alkoxyalkyl designates CH₃OCH₂—; C₃ alkoxyalkyldesignates, for example, CH₃CH(OCH₃)—, CH₃OCH₂CH₂— or CH₃CH₂OCH₂—; andC₄ alkoxyalkyl designates the various isomers of an alkyl groupsubstituted with an alkoxy group containing a total of four carbonatoms, examples including CH₃CH₂CH₂OCH₂— and CH₃CH₂OCH₂CH₂—.

When a compound is substituted with a substituent bearing a subscriptthat indicates the number of said substituents can exceed 1, saidsubstituents (when they exceed 1) are independently selected from thegroup of defined substituents, e.g., (R⁷)_(n), n is 1, 2, 3, 4 or 5).When a group contains a substituent which can be hydrogen, for exampleR² or R³ then when this substituent is taken as hydrogen, it isrecognized that this is equivalent to said group being unsubstituted.When a variable group is shown to be optionally attached to a position,for example (R⁷)_(n) wherein n may be 0, then hydrogen may be at theposition even if not recited in the variable group definition. When oneor more positions on a group are said to be “not substituted” or“unsubstituted”, then hydrogen atoms are attached to take up any freevalency.

The expression “fully saturated” in relation to a ring of atoms meansthat the bonds between the atoms of the ring are all single. Theexpression “fully unsaturated” in relation to a ring means that thebonds between the atoms in the ring are single or double bonds accordingto valence bond theory and furthermore the bonds between the atoms inthe ring include as many double bonds as possible without double bondsbeing cumulative (i.e. no C═C═C, N═C═C, etc.). The term “partiallyunsaturated” in relation to a ring denotes a ring comprising at leastone ring member bonded to an adjacent ring member though a double bondand which conceptually potentially accommodates a number ofnon-cumulated double bonds through adjacent ring members (i.e. in itsfully unsaturated counterpart form) greater than the number of doublebonds present (i.e. in its partially unsaturated form). When a fullyunsaturated ring satisfies Hückel's rule then it can also be describedas aromatic.

Unless otherwise indicated, a “ring” or “ring system” as a component ofFormula 1 (e.g., substituent Q¹) is carbocyclic or heterocyclic. Theterm “ring system” denotes two or more fused rings. The terms “bicyclicring system” and “fused bicyclic ring system” denote a ring systemconsisting of two fused rings, in which either ring can be saturated,partially unsaturated, or fully unsaturated unless otherwise indicated.The term “fused heterobicyclic ring system” denotes a fused bicyclicring system in which at least one ring atom is not carbon.

The term “ring member” refers to an atom or other moiety (e.g., C(═O),C(═S), S(═O) or S(═O)₂) forming the backbone of a ring or ring system.

The terms “carbocyclic ring”, “carbocycle” or “carbocyclic ring system”denote a ring or ring system wherein the atoms forming the ring backboneare selected only from carbon. Unless otherwise indicated, a carbocyclicring can be a saturated, partially unsaturated, or fully unsaturatedring. When a fully unsaturated carbocyclic ring satisfies Hückel's rule,then said ring is also called an “aromatic ring”. “Saturatedcarbocyclic” refers to a ring having a backbone consisting of carbonatoms linked to one another by single bonds; unless otherwise specified,the remaining carbon valences are occupied by hydrogen atoms.

The terms “heterocyclic ring”, “heterocycle” or “heterocyclic ringsystem” denote a ring or ring system in which at least one atom formingthe ring backbone is not carbon, e.g., nitrogen, oxygen or sulfur.Typically a heterocyclic ring contains no more than 5 nitrogens, no morethan 2 oxygens and no more than 2 sulfurs. Unless otherwise indicated, aheterocyclic ring can be a saturated, partially unsaturated, or fullyunsaturated ring. When a fully unsaturated heterocyclic ring satisfiesHückel's rule, then said ring is also called a “heteroaromatic ring” or“aromatic heterocyclic ring”. Unless otherwise indicated, heterocyclicrings and ring systems can be attached through any available carbon ornitrogen by replacement of a hydrogen on said carbon or nitrogen.

“Aromatic” indicates that each of the ring atoms is essentially in thesame plane and has a p-orbital perpendicular to the ring plane, and that(4n+2) π electrons, where n is a positive integer, are associated withthe ring to comply with Hückel's rule. The term “aromatic ring or ringsystem” denotes a carbocyclic or heterocyclic ring or ring system inwhich the ring or at least one ring of the ring system is aromatic. Theterm “aromatic ring or ring system” is also referred to as “aryl”. Theterm “aromatic heterocyclic ring system” denotes a heterocyclic ringsystem in which at least one ring of the ring system is aromatic. Theterm “nonaromatic ring system” denotes a carbocyclic or heterocyclicring system that may be fully saturated, as well as partially or fullyunsaturated, provided that none of the rings in the ring system arearomatic. The term “nonaromatic carbocyclic ring system” describes acarbocyclic ring system in which no ring in the ring system is aromatic.The term “nonaromatic heterocyclic ring system” denotes a heterocyclicring system in which no ring in the ring system is aromatic.

The term “substituted or unsubstituted” or “optionally substituted” inconnection with the heterocyclic rings refers to groups which areunsubstituted or have at least one non-hydrogen substituent that doesnot extinguish the biological activity possessed by the unsubstitutedanalog. As used herein, the following definitions shall apply unlessotherwise indicated. The term “substituted or unsubstituted” is usedinterchangeably with the phrase “optionally substituted” or with theterm “(un)substituted.” Unless otherwise indicated, an optionallysubstituted group may have a substituent at each substitutable positionof the group, and each substitution is independent of the other.

When Q¹ or Q² is 4- to 7-membered heterocyclic ring system, it may beattached to the remainder of Formula 1 though any available carbon ornitrogen ring atom, unless otherwise described. As noted above, Q¹ andQ² can be (among others) phenyl optionally substituted with one or moresubstituents selected from a group of substituents as defined in theSummary of the Invention. An example of phenyl optionally substitutedwith one to five substituents is the ring illustrated as U-1 in Exhibit1, wherein, for example, R^(v) is R¹⁰ as defined in the Summary of theInvention for Q¹, or R^(v) is R¹¹ as defined in the Summary of theInvention for Q², and r is an integer (from 0 to 5).

As noted above, Q¹ and Q² can be (among others) a 5- or 6-memberedunsaturated heterocyclic ring, substituted or unsubstituted with one ormore substituents selected from a group of substituents as defined inthe Summary of the Invention. Examples of a 5- or 6-membered unsaturatedaromatic heterocyclic ring substituted or unsubstituted with from one ormore substituents include the rings U-2 through U-61 illustrated inExhibit 1 wherein R^(v) is any substituent as defined in the Summary ofthe Invention for Q¹ and Q², and r is an integer from 0 to 4, limited bythe number of available positions on each U group. As U-29, U-30, U-36,U-37, U-38, U-39, U-40, U-41, U-42 and U-43 have only one availableposition, for these U groups r is limited to the integers 0 or 1, and rbeing 0 means that the U group is unsubstituted and a hydrogen ispresent at the position indicated by (R^(v))_(r).

Note that when Q¹ or Q² is a 5- or 6-membered saturated or unsaturatednon-aromatic heterocyclic ring optionally substituted with one or moresubstituents selected from the group of substituents as defined in theSummary of the Invention for Q¹ or Q², one or two carbon ring members ofthe heterocycle can optionally be in the oxidized form of a carbonylmoiety.

Examples of a 5- or 6-membered saturated or non-aromatic unsaturatedheterocyclic ring containing ring members selected from up to two Oatoms and up to two S atoms, and optionally substituted on carbon atomring members with up to five substituents as defined in the Summary ofthe Invention includes the rings G-1 through G-35 as illustrated inExhibit 2. Note that when the attachment point on the G group isillustrated as floating, the G group can be attached to the remainder ofFormula 1 through any available carbon or nitrogen of the G group byreplacement of a hydrogen atom. The optional substituents correspondingto R^(v) can be attached to any available carbon or nitrogen byreplacing a hydrogen atom. For these G rings, r is typically an integerfrom 0 to 4, limited by the number of available positions on each Ggroup.

Note that when Q¹ or Q² comprises a ring selected from G-28 throughG-35, G² is selected from O, S or N. Note that when G² is N, thenitrogen atom can complete its valence by substitution with either H orthe substituents corresponding to R^(v) as defined in the Summary of theInvention for Q¹ or Q² (i.e. R¹⁰ or R¹¹ on carbon atoms and R¹² or R¹³on nitrogen atoms).

As noted above, Q¹ or Q² can be (among others) an 8-, 9- or 10-memberedfused bicyclic ring system optionally substituted with one or moresubstituents selected from a group of substituents as defined in theSummary of the Invention (i.e. R¹⁰ or R¹¹ on carbon atoms and R¹² or R¹³on nitrogen atoms). Examples of 8-, 9- or 10-membered fused bicyclicring system optionally substituted with from one or more substituentsinclude the rings U-81 through U-123 illustrated in Exhibit 3 whereinR^(v) is any substituent as defined in the Summary of the Invention forQ¹ or Q² (i.e. R¹⁰ or R¹¹ on carbon atoms and R¹² or R¹³ on nitrogenatoms), and r is typically an integer from 0 to 5.

Although R^(v) groups are shown in the structures U-1 through U-123, itis noted that they do not need to be present since they are optionalsubstituents. Note that when R^(v) is H when attached to an atom, thisis the same as if said atom is unsubstituted. The nitrogen atoms thatrequire substitution to fill their valence are substituted with H orR^(v). Note that when the attachment point between (R^(v))_(r) and the Ugroup is illustrated as floating, (R^(v))_(r) can be attached to anyavailable carbon atom or nitrogen atom of the U group. Note that whenthe attachment point on the U group is illustrated as floating, the Ugroup can be attached to the remainder of Formula 1 through anyavailable carbon or nitrogen of the U group by replacement of a hydrogenatom. Note that some U groups can only be substituted with less than 4R^(v) groups (e.g., U-2 through U-5, U-7 through U-48, and U-52 throughU-61).

A wide variety of synthetic methods are known in the art to enablepreparation of aromatic and nonaromatic heterocyclic rings and ringsystems; for extensive reviews see the eight volume set of ComprehensiveHeterocyclic Chemistry, A. R. Katritzky and C. W. Rees editors-in-chief,Pergamon Press, Oxford, 1984 and the twelve volume set of ComprehensiveHeterocyclic Chemistry II, A. R. Katritzky, C. W. Rees and E. F. V.Scriven editors-in-chief, Pergamon Press, Oxford, 1996.

Compounds of this invention can exist as one or more stereoisomers. Thevarious stereoisomers include enantiomers, diastereomers, atropisomersand geometric isomers. Stereoisomers are isomers of identicalconstitution but differing in the arrangement of their atoms in spaceand include enantiomers, diastereomers, cis-trans isomers (also known asgeometric isomers) and atropisomers. Atropisomers result from restrictedrotation about single bonds where the rotational barrier is high enoughto permit isolation of the isomeric species. One skilled in the art willappreciate that one stereoisomer may be more active and/or may exhibitbeneficial effects when enriched relative to the other stereoisomer(s)or when separated from the other stereoisomer(s). Additionally, theskilled artisan knows how to separate, enrich, and/or to selectivelyprepare said stereoisomers. The compounds of the invention may bepresent as a mixture of stereoisomers, individual stereoisomers or as anoptically active form. Particularly when R⁴ and R⁵ are each H, theC(O)N(Q²)(R⁹) and Q¹ substituents are typically mostly in thethermodynamically preferred trans configuration on the pyrrolidinonering.

For example, as shown in the following, the C(O)N(Q²)(R⁹) moiety (i.e. acompound of Formula 1 wherein both Y¹ and Y² are O; R¹ is H; and J is—CR²R³— and R² and R³ are both H) bonded to the carbon at the 3-positionof the ring and Q¹ bonded to the carbon at the 4-position of the ringare generally found in the trans configuration. These two carbon atomsboth possess a chiral center. The most prevalant pair of enantiomers aredepicted as Formula 1′ and Formula 1″. While this invention pertains toall stereoisomers, the preferred enantiomer for biological operabilityis identified as Formula 1′. For a comprehensive discussion of allaspects of stereoisomerism, see Ernest L. Eliel and Samuel H. Wilen,Stereochemistry of Organic Compounds, John Wiley & Sons, 1994.

The skilled artisan will also recognize that the carbon atom at the5-position of the pyrrolidinone ring (i.e. when J is —CR²R³—, the carbonatom to which both R² and R³ are bonded) also contains a stereocenterindicated by a (*) as shown in Formula 1′″. This invention pertains toall stereoisomers, and therefore, when either R² or R³ are other thanthe same substituent, then a mixture of diastereomers is possible.

Molecular depictions drawn herein follow standard conventions fordepicting stereochemistry. To indicate stereoconfiguration, bonds risingfrom the plane of the drawing and towards the viewer are denoted bysolid wedges wherein the broad end of the wedge is attached to the atomrising from the plane of the drawing towards the viewer. Bonds goingbelow the plane of the drawing and away from the viewer are denoted bydashed wedges wherein the narrow end of the wedge is attached to theatom closer to the viewer. Constant width lines indicate bonds with adirection opposite or neutral relative to bonds shown with solid ordashed wedges; constant width lines also depict bonds in molecules orparts of molecules in which no particular stereoconfiguration isintended to be specified.

This invention also comprises racemic mixtures, for example, equalamounts of the enantiomers of Formulae 1′ and 1″ (and optionally 1′″).In addition, this invention includes compounds that are enrichedcompared to the racemic mixture in an enantiomer of Formula 1.

Also included are the essentially pure enantiomers of compounds ofFormula 1, for example, Formula 1′ and Formula 1″.

When enantiomerically enriched, one enantiomer is present in greateramounts than the other, and the extent of enrichment can be defined byan expression of enantiomeric excess (“ee”), which is defined as (2x−1).100%, where x is the mole fraction of the dominant enantiomer in themixture (e.g., an ee of 20% corresponds to a 60:40 ratio ofenantiomers).

Preferably the compositions of this invention have at least a 50%enantiomeric excess; more preferably at least a 75% enantiomeric excess;still more preferably at least a 90% enantiomeric excess; and the mostpreferably at least a 94% enantiomeric excess of the more active isomer.Of particular note are enantiomerically pure embodiments of the moreactive isomer.

Compounds of Formula 1 can comprise additional chiral centers. Forexample, substituents and other molecular constituents such as R^(A)(i.e as a substituent on L-1) and L-2 through L-4 may themselves containchiral centers. This invention comprises racemic mixtures as well asenriched and essentially pure stereoconfigurations at these additionalchiral centers.

Compounds of this invention can exist as one or more conformationalisomers due to restricted rotation about the amide bond (e.g.,C(O)N(Q²)(R⁹)) in Formula 1. This invention comprises mixtures ofconformational isomers. In addition, this invention includes compoundsthat are enriched in one conformer relative to others.

When enantiomerically enriched, one enantiomer is present in greateramounts than the other, and the extent of enrichment can be defined byan expression of enentiomeric ratio (ER) expressed as the relative area% of the two entantiomers determined by chiral high-performance liquidchromatography.

Preferably the compositions of this invention have at least a 50% ER;more preferably at least a 75% ER; still more preferably at least a 90%ER; and the most preferably at least a 94% ER of the more active isomer.Of particular note are enantiomerically pure embodiments of the moreactive isomer.

Compounds of Formula 1 can comprise additional chiral centers. Forexample, substituents and other molecular constituents such as R², R³and R⁶ may themselves contain chiral centers. This invention comprisesracemic mixtures as well as enriched and essentially purestereoconfigurations at these additional chiral centers.

Compounds of Formula 1 typically exist in more than one form, andFormula 1 thus include all crystalline and non-crystalline forms of thecompounds they represent. Non-crystalline forms include embodimentswhich are solids such as waxes and gums as well as embodiments which areliquids such as solutions and melts. Crystalline forms includeembodiments which represent essentially a single crystal type andembodiments which represent a mixture of polymorphs (i.e. differentcrystalline types). The term “polymorph” refers to a particularcrystalline form of a chemical compound that can crystallize indifferent crystalline forms, these forms having different arrangementsand/or conformations of the molecules in the crystal lattice. Althoughpolymorphs can have the same chemical composition, they can also differin composition due the presence or absence of co-crystallized water orother molecules, which can be weakly or strongly bound in the lattice.Polymorphs can differ in such chemical, physical and biologicalproperties as crystal shape, density, hardness, color, chemicalstability, melting point, hygroscopicity, suspensibility, dissolutionrate and biological availability. One skilled in the art will appreciatethat a polymorph of a compound of Formula 1 can exhibit beneficialeffects (e.g., suitability for preparation of useful formulations,improved biological performance) relative to another polymorph or amixture of polymorphs of the same compound of Formula 1. Preparation andisolation of a particular polymorph of a compound of Formula 1 can beachieved by methods known to those skilled in the art including, forexample, crystallization using selected solvents and temperatures. For acomprehensive discussion of polymorphism see R. Hilfiker, Ed.,Polymorphism in the Pharmaceutical Industry, Wiley-VCH, Weinheim, 2006.

One skilled in the art will appreciate that not all nitrogen-containingheterocycles can form N-oxides since the nitrogen requires an availablelone pair for oxidation to the oxide; one skilled in the art willrecognize those nitrogen-containing heterocycles which can formN-oxides. One skilled in the art will also recognize that tertiaryamines can form N-oxides. Synthetic methods for the preparation ofN-oxides of heterocycles and tertiary amines are very well known by oneskilled in the art including the oxidation of heterocycles and tertiaryamines with peroxy acids such as peracetic and m-chloroperbenzoic acid(MCPBA), hydrogen peroxide, alkyl hydroperoxides such as t-butylhydroperoxide, sodium perborate, and dioxiranes such asdimethyldioxirane. These methods for the preparation of N-oxides havebeen extensively described and reviewed in the literature, see forexample: T. L. Gilchrist in Comprehensive Organic Synthesis, vol. 7, pp748-750, S. V. Ley, Ed., Pergamon Press; M. Tisler and B. Stanovnik inComprehensive Heterocyclic Chemistry, vol. 3, pp 18-20, A. J. Boultonand A. McKillop, Eds., Pergamon Press; M. R. Grimmett and B. R. T. Keenein Advances in Heterocyclic Chemistry, vol. 43, pp 149-161, A. R.Katritzky, Ed., Academic Press; M. Tisler and B. Stanovnik in Advancesin Heterocyclic Chemistry, vol. 9, pp 285-291, A. R. Katritzky and A. J.Boulton, Eds., Academic Press; and G. W. H. Cheeseman and E. S. G.Werstiuk in Advances in Heterocyclic Chemistry, vol. 22, pp 390-392, A.R. Katritzky and A. J. Boulton, Eds., Academic Press.

One skilled in the art recognizes that because in the environment andunder physiological conditions salts of chemical compounds are inequilibrium with their corresponding nonsalt forms, salts share thebiological utility of the nonsalt forms. Thus a wide variety of salts ofa compound of Formula 1 are useful for control of undesired vegetation(i.e. are agriculturally suitable). The salts of a compound of Formula 1include acid-addition salts with inorganic or organic acids such ashydrobromic, hydrochloric, nitric, phosphoric, sulfuric, acetic,butyric, fumaric, lactic, maleic, malonic, oxalic, propionic, salicylic,tartaric, 4-toluenesulfonic or valeric acids. When a compound of Formula1 contains an acidic moiety such as a carboxylic acid or phenol, saltsalso include those formed with organic or inorganic bases such aspyridine, triethylamine or ammonia, or amides, hydrides, hydroxides orcarbonates of sodium, potassium, lithium, calcium, magnesium or barium.Accordingly, the present invention comprises compounds selected fromFormula 1, stereoisomers, N-oxides and agriculturally suitable saltsthereof.

Embodiments of the present invention as described in the Summary of theInvention include where Formula 1 as used in the following Embodimentsincludes N-oxides and salts thereof:

-   -   Embodiment 1. A compound of Formula 1, including all        stereoisomers, N-oxides, and salts thereof, agricultural        compositions containing them and their use as herbicides as        described in the Summary of the Invention.    -   Embodiment 2. A compound of Embodiment 1 wherein L is selected        from L-1, L-2 or L-3.    -   Embodiment 3. A compound of Embodiment 2 wherein L is selected        from L-1 or L-2.    -   Embodiment 4. A compound of Embodiment 3 wherein L is L-1.    -   Embodiment 5. A compound of Embodiment 4 wherein L is L-2.    -   Embodiment 6. A compound of any one of Embodiments 1 through 5        wherein R^(A) is C₁-C₇ alkyl, C₁-C₇ haloalkyl, C₃-C₉ cycloalkyl,        C₁-C₇ alkoxy or C₁-C₇ haloalkoxy, C₃-C₉ cycloalkoxy, each        substituted or unsubstituted with up to 2 substituents        independently selected from R⁸ or G¹; or        -   R^(A) is G¹.    -   Embodiment 7. A compound of Embodiment 6 wherein R^(A) is C₁-C₇        alkyl, C₁-C₇ haloalkyl, C₁-C₇ alkoxy or C₁-C₇ haloalkoxy, each        substituted or unsubstituted with up to 2 substituents        independently selected from R⁸; or        -   R^(A) is G¹.    -   Embodiment 8. A compound of Embodiment 7 wherein R^(A) is C₁-C₇        alkyl or C₁-C₇ alkoxy, each substituted or unsubstituted with up        to 2 substituents independently selected from R⁸.    -   Embodiment 9. A compound of Embodiment 8 wherein R^(A) is C₁-C₃        alkyl, substituted or unsubstituted with up to 2 substituents        independently selected from R⁸.    -   Embodiment 10. A compound of Embodiment 8 wherein R^(A) is C₁-C₃        alkoxy, substituted or unsubstituted with up to 2 substituents        independently selected from R⁸.    -   Embodiment 11. A compound of any one of Embodiments 1 through 4        wherein R^(B) is H, C₁-C₄ alkoxy, C₁-C₄ haloalkyl or C₁-C₄        alkyl.    -   Embodiment 12. A compound of Embodiment 11 wherein R^(B) is H,        —OCH₃, CF₃ or CH₃.    -   Embodiment 13. A compound of Embodiment 12 wherein R^(B) is H,        —OCH₃ or CH₃.    -   Embodiment 14. A compound of Embodiment 13 wherein R^(B) is H.    -   Embodiment 15. A compound of any one of Embodiments 1 through 4        or 11 through 15 wherein R^(C) is H, C₁-C₄ alkoxy, C₁-C₄        haloalkyl or C₁-C₄ alkyl.    -   Embodiment 16. A compound of Embodiment 15 wherein R^(C) is H,        C₁-C₂ alkoxy or C₁-C₂ alkyl.    -   Embodiment 17. A compound of Embodiment 16 wherein R^(C) is H or        CH₃.    -   Embodiment 18. A compound of Embodiment 17 wherein R^(C) is H.    -   Embodiment 19. A compound of Embodiment 18 wherein R^(D) is H,        C₁-C₃ alkyl or C₂-C₃ alkylcarbonyl.    -   Embodiment 20. A compound of Embodiment 19 wherein R^(D) is H,        CH₃, CH₂CH₃ or —C(═O)CH₃.    -   Embodiment 21. A compound of Embodiment 20 wherein R^(D) is H.    -   Embodiment 22. A compound of Embodiment 20 wherein R^(D) is CH₃        or CH₂CH₃.    -   Embodiment 23. A compound of Embodiment 20 wherein R^(D) is        —C(═O)CH₃.    -   Embodiment 24. A compound of any one of Embodiments 1 through 4        or 11 through 23 wherein R^(E) is H, hydroxy, amino, cyano,        formyl, —C(O)NH₂, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₂-C₆        cyanoalkyl, C₃-C₆ cycloalkyl, C₄-C₈ cycloalkylalkyl, C₂-C₈        alkoxyalkyl, C₃-C₈ alkoxyalkoxyalkyl, C₂-C₈ haloalkoxyalkyl,        C₂-C₈ alkenyl, C₂-C₈ haloalkenyl, C₂-C₈ alkenylalkyl, C₂-C₈        haloalkenylalkyl, C₂-C₈ alkylcarbonyl, C₂-C₈ haloalkylcarbonyl,        C₄-C₁₀ cycloalkylcarbonyl, C₅-C₁₀ cycloalkylcarbonylalkyl, C₂-C₈        alkoxycarbonyl, C₂-C₈ haloalkoxycarbonyl, C₄-C₁₀        cycloalkoxycarbonyl, C₂-C₈ alkylaminocarbonyl, C₃-C₁₀        dialkylaminocarbonyl, C₄-C₁₀ cycloalkylaminocarbonyl, C₁-C₆        alkoxy, C₁-C₆ alkylsulfinyl, C₁-C₆ haloalkylsulfinyl, C₃-C₈        cycloalkylsulfinyl, C₁-C₆ alkylsulfonyl, C₁-C₆        haloalkylsulfonyl, C₃-C₈ cycloalkylsulfonyl, C₁-C₆        alkylaminosulfonyl or C₂-C₈ dialkylaminosulfonyl.    -   Embodiment 25. A compound of Embodiment 24 wherein R^(E) is H,        hydroxy, amino, cyano, formyl, —C(O)NH₂, C₁-C₆ alkyl, C₃-C₆        cycloalkyl, C₄-C₈ cycloalkylalkyl, C₂-C₈ alkoxyalkyl, C₃-C₈        alkoxyalkoxyalkyl, C₂-C₈ alkylcarbonyl, C₄-C₁₀        cycloalkylcarbonyl, C₅-C₁₀ cycloalkylcarbonylalkyl, C₂-C₈        alkoxycarbonyl, C₄-C₁₀ cycloalkoxycarbonyl, C₁-C₆ alkylsulfonyl.    -   Embodiment 26. A compound of Embodiment 25 wherein R^(E) is H,        C₁-C₆ alkyl, C₃-C₆ cycloalkyl, C₄-C₈ cycloalkylalkyl, C₂-C₈        alkoxyalkyl, C₂-C₈ alkylcarbonyl, C₂-C₈ alkoxycarbonyl, C₄-C₁₀        cycloalkoxycarbonyl, C₁-C₆ alkylsulfonyl.    -   Embodiment 27. A compound of Embodiment 26 wherein R^(E) is H,        C₁-C₆ alkyl or C₂-C₈ alkylcarbonyl.    -   Embodiment 28. A compound of Embodiment 27 wherein R^(E) is H,        C₁-C₂ alkyl or C₂-C₄ alkylcarbonyl.    -   Embodiment 29. A compound of any one of Embodiments 1, 2 or 11        through 18 wherein R^(F) is formyl, —C(O)NH₂, C₂-C₈        alkylcarbonyl, C₂-C₈ haloalkylcarbonyl, C₄-C₁₀        cycloalkylcarbonyl, C₂-C₈ alkoxycarbonyl, C₂-C₈        haloalkoxycarbonyl, C₄-C₁₀ cycloalkoxycarbonyl, C₂-C₈        alkylaminocarbonyl, C₃-C₁₀ dialkylaminocarbonyl, C₄-C₁₀        cycloalkylaminocarbonyl, C₁-C₆ alkylsulfinyl, C₁-C₆        haloalkylsulfinyl, C₃-C₈ cycloalkylsulfinyl, C₁-C₆        alkylsulfonyl, C₁-C₆ haloalkylsulfonyl, C₃-C₈        cycloalkylsulfonyl, C₁-C₆ alkylaminosulfonyl, C₂-C₈        dialkylaminosulfonyl, —P(═O)(OH)₂, C₁-C₆ dialkylphosphoryl,        C₁-C₆ haloalkylphosphoryl, C₃-C₈ cycloalkylphosphoryl, C₂-C₈        dialkoxyphosphoryl, C₆-C₁₄ dicycloalkoxyphosphoryl, C₈-C₁₆        dicycloalkylalkoxyphosphoryl, C₂-C₁₂ bis(alkylamino)phosphoryl,        C₄-C₂₄ bis(dialkylamino)phosphoryl; or phenyl substituted or        unsubstituted with R¹⁶.    -   Embodiment 30. A compound of Embodiment 29 wherein R^(F) is        C₂-C₈ alkylcarbonyl, C₄-C₁₀ cycloalkylcarbonyl, C₂-C₈        alkoxycarbonyl, C₂-C₈ haloalkoxycarbonyl, C₄-C₁₀        cycloalkoxycarbonyl, C₂-C₈ alkylaminocarbonyl, C₃-C₁₀        dialkylaminocarbonyl, C₄-C₁₀ cycloalkylaminocarbonyl, C₁-C₆        alkylsulfonyl, C₁-C₆ haloalkylsulfonyl, C₃-C₈ cycloalkylsulfonyl        or C₁-C₆ alkylaminosulfonyl; or phenyl substituted or        unsubstituted with R¹⁶.    -   Embodiment 31. A compound of Embodiment 30 wherein R^(F) is        C₂-C₈ alkylcarbonyl, C₂-C₈ alkoxycarbonyl, C₂-C₈        haloalkoxycarbonyl, C₂-C₈ alkylaminocarbonyl, C₃-C₁₀        dialkylaminocarbonyl or C₁-C₆ alkylsulfonyl.    -   Embodiment 32. A compound of Embodiment 31 wherein R^(F) is        C₂-C₄ alkylcarbonyl or C₂-C₄ alkoxycarbonyl.    -   Embodiment 33. A compound of any one of Embodiments 1 through 3        or 11 through 18 wherein R^(G) is formyl, —C(O)NH₂, C₂-C₈        alkylcarbonyl, C₂-C₈ haloalkylcarbonyl, C₄-C₁₀        cycloalkylcarbonyl, C₂-C₈ alkoxycarbonyl, C₂-C₈        haloalkoxycarbonyl, C₄-C₁₀ cycloalkoxycarbonyl, C₂-C₈        alkylaminocarbonyl, C₃-C₁₀ dialkylaminocarbonyl, C₄-C₁₀        cycloalkylaminocarbonyl, C₁-C₆ alkylsulfinyl, C₁-C₆        haloalkylsulfinyl, C₃-C₈ cycloalkylsulfinyl, C₁-C₆        alkylsulfonyl, C₁-C₆ haloalkylsulfonyl, C₃-C₈ cycloalkylsulfonyl        or C₁-C₆ alkylaminosulfonyl.    -   Embodiment 34. A compound of Embodiment 33 wherein R^(G) is        formyl, C₂-C₈ alkylcarbonyl, C₂-C₈ alkoxycarbonyl, C₄-C₁₀        cycloalkoxycarbonyl, C₂-C₈ alkylaminocarbonyl, C₄-C₁₀        cycloalkylaminocarbonyl, C₁-C₆ alkylsulfonyl, C₁-C₆        haloalkylsulfonyl, C₃-C₈ cycloalkylsulfonyl or C₁-C₆        alkylaminosulfonyl.    -   Embodiment 35. A compound of Embodiment 34 wherein R^(G) is        formyl, C₂-C₈ alkylcarbonyl, C₂-C₈ alkoxycarbonyl or C₄-C₁₀        cycloalkoxycarbonyl.    -   Embodiment 36. A compound of Embodiment 35 wherein R^(G) is        C₂-C₈ alkylcarbonyl or C₂-C₈ alkoxycarbonyl.    -   Embodiment 37. A compound of Embodiment 36 wherein R^(G) is        C₂-C₄ alkylcarbonyl or C₂-C₄ alkoxycarbonyl.    -   Embodiment 38. A compound of any one of Embodiments 1 through 11        wherein each R⁸ is independently cyano, nitro, —CHO, C₂-C₆        alkenyl, C₂-C₆ alkynyl, C₂-C₈ alkylcarbonyl, C₂-C₈        haloalkylcarbonyl, C₂-C₈ alkoxycarbonyl, C₄-C₁₀        cycloalkoxycarbonyl, C₅-C₁₂ cycloalkylalkoxycarbonyl, C₂-C₈        alkylaminocarbonyl, C₃-C₁₀ dialkylaminocarbonyl, C₁-C₆ alkoxy,        C₁-C₆ haloalkoxy or C₂-C₈ alkylcarbonyloxy.    -   Embodiment 39. A compound of Embodiment 38 wherein each R⁸ is        independently C₂-C₆ alkenyl, C₁-C₆ alkoxy or C₁-C₆ haloalkoxy.    -   Embodiment 40. A compound of Embodiment 39 wherein each R⁸ is        independently C₁-C₆ alkoxy or C₁-C₆ haloalkoxy.    -   Embodiment 40A. A compound of Embodiment 40 wherein each R⁸ is        independently C₁-C₆ alkoxy.    -   Embodiment 41. A compound of any one of Embodiments 1 through        40A wherein J is —CR²R³—, —CR²R³—CR⁴R⁵— or —NR⁶—.    -   Embodiment 42. A compound of Embodiment 41 wherein J is —CR²R³—        or —CR²R³—CR⁴R⁵—.    -   Embodiment 43. A compound of Embodiment 42 wherein J is        —CR²R³—CR⁴R⁵—.    -   Embodiment 44. A compound of Embodiment 43 wherein J is —CR²R³—.    -   Embodiment 45. A compound of any one of Embodiments 1 through 44        wherein Y¹ and Y² are each independently O or S.    -   Embodiment 46. A compound of Embodiment 45 wherein Y¹ and Y² are        each independently S.    -   Embodiment 47. A compound of Embodiment 46 wherein Y¹ and Y² are        each independently O.    -   Embodiment 48. A compound of any one of Embodiments 1 through 47        wherein R¹ is H, CHO, C₃-C₈ alkylcarbonylalkyl, C₁-C₆ alkyl,        C₁-C₆ haloalkyl, C₂-C₆ alkenyl, C₃-C₆ alkynyl, C₂-C₆ cyanoalkyl,        C₃-C₆ cycloalkyl, C₄-C₈ cycloalkylalkyl, C₂-C₈ alkoxyalkyl,        C₃-C₈ alkoxyalkoxyalkyl, C₂-C₈ haloalkoxyalkyl, C₂-C₈        alkylthioalkyl, C₂-C₈ alkylcarbonyl, C₂-C₈ haloalkylcarbonyl,        C₄-C₁₀ cycloalkylcarbonyl, C₂-C₈ alkoxycarbonyl, C₂-C₈        haloalkoxycarbonyl, C₂-C₈ alkylaminocarbonyl, C₃-C₁₀        dialkylaminocarbonyl or C₄-C₁₀ cycloalkylaminocarbonyl.    -   Embodiment 49. A compound of Embodiment 48 wherein R¹ is H,        C₃-C₈ alkylcarbonylalkyl, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₂-C₆        cyanoalkyl, C₃-C₆ cycloalkyl, C₄-C₈ cycloalkylalkyl, C₂-C₈        alkoxyalkyl, C₂-C₈ haloalkoxyalkyl, C₂-C₈ alkylcarbonyl, C₂-C₈        haloalkylcarbonyl, C₄-C₁₀ cycloalkylcarbonyl, C₂-C₈        alkoxycarbonyl or C₂-C₈ haloalkoxycarbonyl.    -   Embodiment 50. A compound of Embodiment 49 wherein R¹ is H,        C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₂-C₆ cyanoalkyl, C₃-C₆        cycloalkyl, C₄-C₈ cycloalkylalkyl, C₂-C₈ alkoxyalkyl, C₂-C₈        haloalkoxyalkyl or C₂-C₈ alkoxycarbonyl.    -   Embodiment 51. A compound of Embodiment 50 wherein R¹ is H,        C₁-C₆ alkyl, C₃-C₆ cycloalkyl, C₄-C₈ cycloalkylalkyl or C₂-C₈        alkoxyalkyl.    -   Embodiment 52. A compound of Embodiment 51 wherein R¹ is H, CH₃,        CH₂CH₃, cyclopropyl, cyclopropylmethyl or CH₂OCH₃.    -   Embodiment 53. A compound of any one of Embodiments 1 through 52        wherein Q¹ is a phenyl ring or a naphthalenyl ring system, each        ring or ring system substituted or unsubstituted with up to 5        substituents independently selected from R¹⁰; or a 5- to        6-membered heterocyclic ring; or an 8- to 10-membered bicyclic        ring system, each ring or ring system containing ring members        selected from carbon atoms and 1 to 4 heteroatoms independently        selected from up to 2 O, up to 2 S and up to 4 N atoms, wherein        up to 2 carbon ring members are independently selected from        C(═O) and C(═S), and the sulfur atom ring members are        independently selected from S(═O)_(u)(═NR¹⁴)_(v), each ring or        ring system substituted or unsubstituted with up to 4        substituents independently selected from R¹⁰ on carbon atom ring        members and selected from R¹² on nitrogen atom ring members.    -   Embodiment 54. A compound of Embodiment 53 wherein Q¹ is a        phenyl ring substituted or unsubstituted with up to 4        substituents independently selected from R¹⁰; or a 5- to        6-membered heterocyclic ring, each ring containing ring members        selected from carbon atoms and 1 to 4 heteroatoms independently        selected from up to 2 O, up to 2 S and up to 4 N atoms, each        ring substituted or unsubstituted with up to 4 substituents        independently selected from R¹⁰ on carbon atom ring members and        selected from R¹² on nitrogen atom ring members.    -   Embodiment 55. A compound of Embodiment 54 wherein Q¹ is a        phenyl ring substituted or unsubstituted with up to 4        substituents independently selected from R¹⁰.    -   Embodiment 56. A compound of Embodiment 55 wherein Q¹ is a        phenyl ring substituted or unsubstituted with up to 3        substituents independently selected from R¹⁰.    -   Embodiment 57. A compound of Embodiment 56 wherein Q¹ is a        phenyl ring substituted or unsubstituted with up to 2        substituents independently selected from R¹⁰.    -   Embodiment 58. A compound of Embodiment 57 wherein Q¹ is a        phenyl ring substituted with up 2 substituents independently        selected from R¹⁰.    -   Embodiment 59. A compound of Embodiment 58 wherein Q¹ is a        phenyl ring substituted with up 2 substituents independently        selected from R¹⁰ where one substituent is at the para (4-)        position.    -   Embodiment 60. A compound of Embodiment 59 wherein Q¹ is a        phenyl ring substituted with up 2 substituents independently        selected from R¹⁰ where one substituent is at the meta (3-)        position.    -   Embodiment 61. A compound of any one of Embodiments 1 through 60        wherein Q¹ is other than an unsubstituted phenyl ring.    -   Embodiment 62. A compound of Embodiment 61 wherein Q¹ is an 8-        to 10-membered bicyclic ring system containing ring members        selected from carbon atoms and 1 to 4 heteroatoms independently        selected from up to 2 O atoms, each ring system optionally        substituted with up to 4 substituents independently selected        from R¹⁰ on carbon atom ring members.    -   Embodiment 63. A compound of Embodiment 62 wherein Q¹ is a        9-membered bicyclic ring system containing ring members selected        from carbon atoms and 1 to 4 heteroatoms independently selected        from up to 2 O atoms, each ring system optionally substituted        with up to 4 substituents independently selected from R¹⁰ on        carbon atom ring members.    -   Embodiment 64. A compound of Embodiment 63 wherein Q¹ is a        9-membered heteroaromatic bicyclic ring system containing ring        members selected from carbon atoms and 2 O atoms, system        optionally substituted with up to 3 substituents independently        selected from R¹⁰ on carbon atom ring members (i.e. U-103 in        Exhibit 3).    -   Embodiment 65. A compound of Embodiment 64 wherein Q¹ is U-103A:

-   -   Embodiment 66. A compound of any one of Embodiments 1 through 65        wherein Q² is a phenyl ring, each ring substituted or        unsubstituted with up to 4 substituents independently selected        from R¹¹; or a 5- to 6-membered heterocyclic ring; or an 8- to        10-membered bicyclic ring system, each ring or ring system        containing ring members selected from carbon atoms and 1 to 4        heteroatoms independently selected from up to 2 O, up to 2 S and        up to 4 N atoms, wherein up to 2 carbon ring members are        independently selected from C(═O) and C(═S), and the sulfur atom        ring members are independently selected from        S(═O)_(u)(═NR¹⁴)_(v), each ring or ring system substituted or        unsubstituted with up to 4 substituents independently selected        from R¹¹ on carbon atom ring members and selected from R¹³ on        nitrogen atom ring members.    -   Embodiment 67. A compound of Embodiment 66 wherein Q² is a        phenyl ring, substituted or unsubstituted with up to 4        substituents independently selected from R¹¹; or a 5- to        6-membered heterocyclic ring; or an 8- to 10-membered bicyclic        ring system, each ring or ring system containing ring members        selected from carbon atoms and 1 to 4 heteroatoms independently        selected from up to 2 O, up to 2 S and up to 4 N atoms, wherein        up to 2 carbon ring members are independently selected from        C(═O) and C(═S), and the sulfur atom ring members are        independently selected from S(═O)_(u)(═NR¹⁴)_(v), each ring or        ring system substituted or unsubstituted with up to 4        substituents independently selected from R¹¹ on carbon atom ring        members and selected from R¹³ on nitrogen atom ring members.    -   Embodiment 68. A compound of Embodiment 67 wherein Q² is a        phenyl ring, substituted or unsubstituted with up to 4        substituents independently selected from R¹¹; or a 5- to        6-membered heterocyclic ring containing ring members selected        from carbon atoms and 1 to 4 heteroatoms independently selected        from up to 4 N atoms, wherein up to 2 carbon ring members are        independently selected from C(═O) and C(═S), each ring or ring        system substituted or unsubstituted with up to 4 substituents        independently selected from R¹¹ on carbon atom ring members and        selected from R¹³ on nitrogen atom ring members.    -   Embodiment 69. A compound of Embodiment 68 wherein Q² is a        phenyl ring, substituted or unsubstituted with up to 4        substituents independently selected from R¹¹.    -   Embodiment 70. A compound of Embodiment 69 wherein Q² is a        phenyl ring, substituted or unsubstituted with up to 3        substituents independently selected from R¹¹.    -   Embodiment 71. A compound of Embodiment 70 wherein Q² is a        phenyl ring, substituted or unsubstituted with up to 2        substituents independently selected from R¹¹.    -   Embodiment 72. A compound of Embodiment 71 wherein Q² is a        phenyl ring, substituted with at least 2 substituents        independently selected from R¹¹ where one substituent is at the        ortho (2-) position.    -   Embodiment 73. A compound of Embodiment 72 wherein Q² is a        phenyl ring, substituted with at least 2 substituents        independently selected from R¹¹ where one substituent is at the        meta (3-) position.    -   Embodiment 74. A compound of any one of Embodiments 1 through 73        wherein Q² is other than an unsubstituted phenyl ring.    -   Embodiment 75. A compound of any one of Embodiments 1 through 74        wherein R² and R³ are each independently H or C₁-C₄ alkyl.    -   Embodiment 76. A compound of Embodiment 75 wherein R² and R³ are        each independently H or CH₃.    -   Embodiment 77. A compound of Embodiment 76 wherein R² and R³ are        each independently H.    -   Embodiment 78. A compound of any one of Embodiments 1 through 77        wherein R⁴ and R⁵ are each independently H, halogen, C₁-C₄ alkyl        or C₁-C₄ alkoxy.    -   Embodiment 79. A compound of Embodiment 78 wherein R⁴ and R⁵ are        each independently H, halogen or C₁-C₄ alkyl.    -   Embodiment 80. A compound of Embodiment 79 wherein R⁴ and R⁵ are        each independently H, Cl or CH₃.    -   Embodiment 81. A compound of any one of Embodiments 1 through 80        wherein R⁶ is H, C₁-C₆ alkyl or C₁-C₆ alkoxy.    -   Embodiment 82. A compound of Embodiment 81 wherein R⁶ is H or        C₁-C₆ alkyl.    -   Embodiment 83. A compound of Embodiment 82 wherein R⁶ is H or        CH₃.    -   Embodiment 84. A compound of Embodiment 83 wherein R⁶ is H.    -   Embodiment 85. A compound of any one of Embodiments 1 through 47        or 53 through 84 wherein R¹ and R⁶ are taken together as C₃        alkylene or —CH₂OCH₂—.    -   Embodiment 86. A compound of Embodiment 85 wherein R¹ and R⁶ are        taken together as C₃ alkylene.    -   Embodiment 87. A compound of any one of Embodiments 1 through 86        wherein R⁷ is H, halogen, C₁-C₄ alkoxy or C₁-C₄ alkyl.    -   Embodiment 88. A compound of Embodiment 87 wherein R⁷ is H, F,        Cl or CH₃.    -   Embodiment 89. A compound of any one of Embodiments 1 through 88        wherein R⁷ is H or CH₃.    -   Embodiment 90. A compound of Embodiment 89 wherein R⁷ is H.    -   Embodiment 91. A compound of any one of Embodiments 1 through 90        wherein R⁹ is H, C₁-C₆ alkyl, C₂-C₈ alkoxyalkyl, C₂-C₈        alkylthioalkyl, C₂-C₈ alkylsulfinylalkyl, C₂-C₈        alkylsulfonylalkyl, C₂-C₈ alkylcarbonyl, C₄-C₁₀        cycloalkylcarbonyl, C₂-C₈ alkoxycarbonyl or C₄-C₁₀        cycloalkoxycarbonyl.    -   Embodiment 92. A compound of Embodiment 91 wherein R⁹ is H,        C₁-C₆ alkyl, C₂-C₈ alkoxyalkyl, C₂-C₈ alkylcarbonyl or C₂-C₈        alkoxycarbonyl.    -   Embodiment 93. A compound of Embodiment 92 wherein R⁹ is H,        C₁-C₆ alkyl or C₂-C₈ alkoxycarbonyl.    -   Embodiment 94. A compound of Embodiment 93 wherein R⁹ is H, CH₃        or —C(═O)CH₃.    -   Embodiment 95. A compound of Embodiment 94 wherein R⁹ is H.    -   Embodiment 96. A compound of any one of Embodiments 1 through 95        wherein each R¹⁰ and R¹¹ is halogen, nitro, C₁-C₈ alkyl, C₁-C₈        cyanoalkyl, C₁-C₈ cyanoalkoxy, C₁-C₈ haloalkyl, C₁-C₈        nitroalkyl, C₂-C₈ alkenyl, C₂-C₈ haloalkenyl, C₂-C₈        nitroalkenyl, C₂-C₈ alkoxyalkyl, C₃-C₈ alkoxyalkoxyalkyl, C₂-C₈        haloalkoxyalkyl, C₂-C₈ haloalkoxyhaloalkoxy, C₄-C₁₀        cycloalkylalkyl, C₄-C₁₀ halocycloalkylalkyl, C₅-C₁₂        alkylcycloalkylalkyl, C₅-C₁₂ cycloalkylalkenyl, C₃-C₈        cycloalkyl, C₃-C₈ halocycloalkyl, C₄-C₁₀ alkylcycloalkyl, C₆-C₁₂        cycloalkylcycloalkyl, C₃-C₈ cycloalkenyl, C₃-C₈        halocycloalkenyl, C₂-C₈ haloalkoxyalkoxy, C₂-C₈ alkoxyalkoxy,        C₄-C₁₀ cycloalkoxyalkyl, C₂-C₈ alkylcarbonyl, C₂-C₈        haloalkylcarbonyl, C₄-C₁₀ cycloalkylcarbonyl, —C(═O)OH, C₂-C₈        alkoxycarbonyl, C₂-C₈ haloalkoxycarbonyl, C₄-C₁₀        cycloalkoxycarbonyl, C₅-C₁₂ cycloalkylalkoxycarbonyl, —C(═O)NH₂,        C₁-C₈ alkoxy, C₁-C₈ haloalkoxy, C₂-C₈ alkenyloxy, C₂-C₈        haloalkenyloxy, C₃-C₈ cycloalkoxy, C₃-C₈ halocycloalkoxy, C₄-C₁₀        cycloalkylalkoxy, C₃-C₁₀ alkylcarbonylalkoxy, C₂-C₈        alkylcarbonyloxy, C₂-C₈ haloalkylcarbonyloxy, C₄-C₁₀        cycloalkylcarbonyloxy, C₁-C₈ alkylsulfonyloxy, C₁-C₈        haloalkylsulfonyloxy, C₁-C₈ alkylsulfonyl, C₁-C₈        haloalkylsulfonyl, C₃-C₈ cycloalkylsulfonyl.    -   Embodiment 97. A compound of Embodiment 96 wherein each R¹⁰ and        R¹¹ is independently halogen, C₁-C₈ alkyl, C₁-C₈ haloalkyl,        C₂-C₈ alkoxyalkyl, C₃-C₈ alkoxyalkoxyalkyl, C₄-C₁₀        cycloalkylalkyl, C₅-C₁₂ alkylcycloalkylalkyl, C₃-C₈ cycloalkyl,        C₃-C₈ halocycloalkyl, C₆-C₁₂ cycloalkylcycloalkyl, C₃-C₈        halocycloalkenyl, C₂-C₈ haloalkoxyalkoxy, C₂-C₈ alkoxyalkoxy,        C₄-C₁₀ cycloalkoxyalkyl, C₂-C₈ alkylcarbonyl, C₂-C₈        haloalkylcarbonyl, C₄-C₁₀ cycloalkylcarbonyl, C₂-C₈        alkoxycarbonyl, C₄-C₁₀ cycloalkoxycarbonyl, C₅-C₁₂        cycloalkylalkoxycarbonyl, C₁-C₈ alkoxy, C₁-C₈ haloalkoxy, C₂-C₈        haloalkenyloxy, C₃-C₈ cycloalkoxy, C₃-C₈ halocycloalkoxy, C₄-C₁₀        cycloalkylalkoxy, C₃-C₁₀ alkylcarbonylalkoxy or C₂-C₈        haloalkylcarbonyloxy.    -   Embodiment 98. A compound of Embodiment 97 wherein each R¹⁰ and        R¹¹ is independently halogen, C₁-C₈ alkyl, C₁-C₈ haloalkyl,        C₂-C₈ alkoxyalkyl, C₄-C₁₀ cycloalkylalkyl, C₅-C₁₂        alkylcycloalkylalkyl, C₃-C₈ cycloalkyl, C₃-C₈ halocycloalkyl,        C₂-C₈ haloalkoxyalkoxy, C₁-C₈ alkoxy, C₁-C₈ haloalkoxy or C₂-C₈        alkoxyalkoxy.    -   Embodiment 99. A compound of Embodiment 98 wherein each R¹⁰ and        R¹¹ is independently halogen, C₁-C₈ alkyl, C₁-C₈ haloalkyl,        C₃-C₈ cycloalkyl, C₁-C₈ alkoxy or C₁-C₈ haloalkoxy.    -   Embodiment 100. A compound of Embodiment 99 wherein each R¹⁰ and        R¹¹ is independently halogen, C₁-C₈ alkyl, C₁-C₈ haloalkyl,        C₁-C₈ alkoxy or C₁-C₈ haloalkoxy.    -   Embodiment 101. A compound of Embodiment 100 wherein each R¹⁰        and R¹¹ is independently halogen or C₁-C₈ alkyl.    -   Embodiment 102. A compound of Embodiment 100 wherein each R¹⁰        and R¹¹ is independently halogen or C₁-C₈ haloalkyl.    -   Embodiment 103. A compound of Embodiment 100 wherein each R¹⁰        and R¹¹ is independently halogen or C₁-C₈ alkoxy.    -   Embodiment 104. A compound of Embodiment 100 wherein each R¹⁰        and R¹¹ is independently halogen or C₁-C₈ haloalkoxy.    -   Embodiment 105. A compound of Embodiment 100 wherein each R¹⁰        and R¹¹ is independently C₁-C₈ alkyl or C₁-C₈ alkoxy.    -   Embodiment 106. A compound of Embodiment 100 wherein each R¹⁰        and R¹¹ is independently C₁-C₈ alkyl or C₁-C₈ haloalkyl.    -   Embodiment 107. A compound of any one of Embodiments 1 through        106 wherein each R¹² and R¹³ is independently C₁-C₃ alkyl, C₂-C₃        alkenyl, C₃-C₆ cycloalkyl, C₂-C₃ alkoxyalkyl, C₂-C₃        alkylcarbonyl or C₂-C₃ alkylaminoalkyl.    -   Embodiment 108. A compound of Embodiment 107 wherein each R¹²        and R¹³ is independently C₁-C₃ alkyl, C₃-C₆ cycloalkyl or C₂-C₃        alkylcarbonyl.    -   Embodiment 109. A compound of Embodiment 108 wherein each R¹²        and R¹³ is independently C₁-C₃ alkyl or C₂-C₃ alkylcarbonyl.    -   Embodiment 110. A compound of Embodiment 109 wherein each R¹²        and R¹³ is independently C₁-C₃ alkyl.    -   Embodiment 111. A compound of Embodiment 110 wherein each R¹²        and R¹³ is independently CH₃.    -   Embodiment 112. A compound of any one of Embodiments 1 through        111 wherein each R¹⁴ is independently H or —(C═O)CH₃.    -   Embodiment 113. A compound of Embodiment 112 wherein each R¹⁴ is        independently H.    -   Embodiment 114. A compound of any one of Embodiments 1 through        113 wherein R¹⁵ is H, CHO, C₁-C₄ alkyl, C₂-C₆ alkylcarbonyl or        C₂-C₆ haloalkylcarbonyl.    -   Embodiment 115. A compound of Embodiment 114 wherein R¹⁵ is H,        CH₃, —(C═O)CH₃ or —(C═O)CF₃.    -   Embodiment 116. A compound of Embodiment 115 wherein each R¹⁵ is        independently H or CH₃.    -   Embodiment 117. A compound of any one of Embodiments 1 through        116 wherein each G¹ is independently phenyl; or a 6-membered        heterocyclic ring, each substituted or unsubstituted on ring        members with up to 4 substituents independently selected from        R¹⁷.    -   Embodiment 118. A compound of Embodiment 117 wherein each G¹ is        independently phenyl substituted or unsubstituted on ring        members with up to 3 substituents independently selected from        R¹⁷.    -   Embodiment 119. A compound of any one of Embodiments 1 through        118 wherein each R¹⁶, R¹⁷ and R¹⁸ is independently halogen,        cyano, hydroxy, amino, nitro, —CHO, —C(═O)OH, —C(═O)NH₂,        —SO₂NH₂, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₂-C₆ alkenyl, C₂-C₆        alkynyl, C₂-C₈ alkylcarbonyl, C₁-C₈ hydroxyalkyl, C₂-C₈        haloalkylcarbonyl, C₂-C₆ alkoxyalkyl, C₂-C₆ alkylaminoalkyl,        C₂-C₈ alkoxycarbonyl, C₃-C₈ cycloalkyl, C₄-C₁₀        cycloalkoxycarbonyl, C₅-C₁₂ cycloalkylalkoxycarbonyl, C₂-C₈        alkylaminocarbonyl, C₃-C₁₀ dialkylaminocarbonyl, C₃-C₈        dialkylaminoalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, C₂-C₈        alkylcarbonyloxy or C₁-C₆ alkylthio.    -   Embodiment 120. A compound of Embodiment 119 wherein each R¹⁶,        R¹⁷ and R¹⁸ is independently halogen, cyano, hydroxy, amino,        nitro, —CHO, —C(═O)OH, —C(═O)NH₂, —SO₂NH₂, C₁-C₆ alkyl or C₁-C₆        haloalkyl.    -   Embodiment 121. A compound of Embodiment 120 wherein each R¹⁶,        R¹⁷ and R¹⁸ is independently halogen, nitro, C₁-C₆ alkyl or        C₁-C₆ haloalkyl.    -   Embodiment 122. A compound of Embodiment 121 wherein each R¹⁶,        R¹⁷ and R¹⁸ is independently halogen, C₁-C₆ alkyl or C₁-C₆        haloalkyl.    -   Embodiment 123. A compound of Embodiment 122 wherein each R¹⁶,        R¹⁷ and R¹⁸ is independently halogen or C₁-C₆ alkyl.    -   Embodiment 124. A compound of Embodiment 123 wherein each R¹⁶,        R¹⁷ and R¹⁸ is independently halogen.    -   Embodiment 125. A compound of any one of Embodiments 1 through        124 provided the sum of u and v is 0.    -   Embodiment 126. A compound of any one of Embodiments 1 through        125 provided the sum of u and v is 2.

Embodiments of this invention, including Embodiments 1-126 above as wellas any other embodiments described herein, can be combined in anymanner, and the descriptions of variables in the embodiments pertain notonly to the compounds of Formula 1 but also to the starting compoundsand intermediate compounds useful for preparing the compounds ofFormula 1. In addition, embodiments of this invention, includingEmbodiments 1-126 above as well as any other embodiments describedherein, and any combination thereof, pertain to the compositions andmethods of the present invention.

Embodiment A. A compound of Summary of the Invention 1 wherein:

-   -   R^(A) is C₁-C₇ alkyl, C₁-C₇ haloalkyl, C₃-C₉ cycloalkyl, C₁-C₇        alkoxy or C₁-C₇ haloalkoxy, C₃-C₉ cycloalkoxy, each substituted        or unsubstituted with up to 2 substituents independently        selected from R⁸ or G¹; or    -   R^(A) is G¹;    -   R^(B) is H, C₁-C₄ alkoxy, C₁-C₄ haloalkyl or C₁-C₄ alkyl;    -   R^(C) is H, C₁-C₄ alkoxy, C₁-C₄ haloalkyl or C₁-C₄ alkyl;    -   R^(D) is H, C₁-C₃ alkyl or C₂-C₃ alkylcarbonyl;    -   R^(E) is H, hydroxy, amino, cyano, formyl, —C(O)NH₂, C₁-C₆        alkyl, C₁-C₆ haloalkyl, C₂-C₆ cyanoalkyl, C₃-C₆ cycloalkyl,        C₄-C₈ cycloalkylalkyl, C₂-C₈ alkoxyalkyl, C₃-C₈        alkoxyalkoxyalkyl, C₂-C₈ haloalkoxyalkyl, C₂-C₈ alkenyl, C₂-C₈        haloalkenyl, C₂-C₈ alkenylalkyl, C₂-C₈ haloalkenylalkyl, C₂-C₈        alkylcarbonyl, C₂-C₈ haloalkylcarbonyl, C₄-C₁₀        cycloalkylcarbonyl, C₅-C₁₀ cycloalkylcarbonylalkyl, C₂-C₈        alkoxycarbonyl, C₂-C₈ haloalkoxycarbonyl, C₄-C₁₀        cycloalkoxycarbonyl, C₂-C₈ alkylaminocarbonyl, C₃-C₁₀        dialkylaminocarbonyl, C₄-C₁₀ cycloalkylaminocarbonyl, C₁-C₆        alkoxy, C₁-C₆ alkylsulfinyl, C₁-C₆ haloalkylsulfinyl, C₃-C₈        cycloalkylsulfinyl, C₁-C₆ alkylsulfonyl, C₁-C₆        haloalkylsulfonyl, C₃-C₈ cycloalkylsulfonyl, C₁-C₆        alkylaminosulfonyl or C₂-C₈ dialkylaminosulfonyl;    -   R^(F) is formyl, —C(O)NH₂, C₂-C₈ alkylcarbonyl, C₂-C₈        haloalkylcarbonyl, C₄-C₁₀ cycloalkylcarbonyl, C₂-C₈        alkoxycarbonyl, C₂-C₈ haloalkoxycarbonyl, C₄-C₁₀        cycloalkoxycarbonyl, C₂-C₈ alkylaminocarbonyl, C₃-C₁₀        dialkylaminocarbonyl, C₄-C₁₀ cycloalkylaminocarbonyl, C₁-C₆        alkylsulfinyl, C₁-C₆ haloalkylsulfinyl, C₃-C₈        cycloalkylsulfinyl, C₁-C₆ alkylsulfonyl, C₁-C₆        haloalkylsulfonyl, C₃-C₈ cycloalkylsulfonyl, C₁-C₆        alkylaminosulfonyl, C₂-C₈ dialkylaminosulfonyl, —P(═O)(OH)₂,        C₁-C₆ dialkylphosphoryl, C₁-C₆ haloalkylphosphoryl, C₃-C₈        cycloalkylphosphoryl, C₂-C₈ dialkoxyphosphoryl, C₆-C₁₄        dicycloalkoxyphosphoryl, C₈-C₁₆ dicycloalkylalkoxyphosphoryl,        C₂-C₁₂ bis(alkylamino)phosphoryl, C₄-C₂₄        bis(dialkylamino)phosphoryl; or phenyl substituted or        unsubstituted with R¹⁶;    -   R^(G) is formyl, —C(O)NH₂, C₂-C₈ alkylcarbonyl, C₂-C₈        haloalkylcarbonyl, C₄-C₁₀ cycloalkylcarbonyl, C₂-C₈        alkoxycarbonyl, C₂-C₈ haloalkoxycarbonyl, C₄-C₁₀        cycloalkoxycarbonyl, C₂-C₈ alkylaminocarbonyl, C₃-C₁₀        dialkylaminocarbonyl, C₄-C₁₀ cycloalkylaminocarbonyl, C₁-C₆        alkylsulfinyl, C₁-C₆ haloalkylsulfinyl, C₃-C₈        cycloalkylsulfinyl, C₁-C₆ alkylsulfonyl, C₁-C₆        haloalkylsulfonyl, C₃-C₈ cycloalkylsulfonyl or C₁-C₆        alkylaminosulfonyl;    -   Q¹ is a phenyl ring or a naphthalenyl ring system, each ring or        ring system substituted or unsubstituted with up to 5        substituents independently selected from R¹⁰; or a 5- to        6-membered heterocyclic ring; or an 8- to 10-membered bicyclic        ring system, each ring or ring system containing ring members        selected from carbon atoms and 1 to 4 heteroatoms independently        selected from up to 2 O, up to 2 S and up to 4 N atoms, wherein        up to 2 carbon ring members are independently selected from        C(═O) and C(═S), and the sulfur atom ring members are        independently selected from S(═O)_(u)(═NR¹⁴)_(v), each ring or        ring system substituted or unsubstituted with up to 4        substituents independently selected from R¹⁰ on carbon atom ring        members and selected from R¹² on nitrogen atom ring members;    -   Q² is a phenyl ring, each ring substituted or unsubstituted with        up to 4 substituents independently selected from R¹¹; or a 5- to        6-membered heterocyclic ring; or an 8- to 10-membered bicyclic        ring system, each ring or ring system containing ring members        selected from carbon atoms and 1 to 4 heteroatoms independently        selected from up to 2 O, up to 2 S and up to 4 N atoms, wherein        up to 2 carbon ring members are independently selected from        C(═O) and C(═S), and the sulfur atom ring members are        independently selected from S(═O)_(u)(═NR¹⁴)_(v), each ring or        ring system substituted or unsubstituted with up to 4        substituents independently selected from R¹¹ on carbon atom ring        members and selected from R¹³ on nitrogen atom ring members;    -   J is —CR²R³—, —CR²R³—CR⁴R⁵— or —NR⁶—;    -   Y¹ and Y² are each independently O or S;    -   R¹ is H, CHO, C₃-C₈ alkylcarbonylalkyl, C₁-C₆ alkyl, C₁-C₆        haloalkyl, C₂-C₆ alkenyl, C₃-C₆ alkynyl, C₂-C₆ cyanoalkyl, C₃-C₆        cycloalkyl, C₄-C₈ cycloalkylalkyl, C₂-C₈ alkoxyalkyl, C₃-C₈        alkoxyalkoxyalkyl, C₂-C₈ haloalkoxyalkyl, C₂-C₈ alkylthioalkyl,        C₂-C₈ alkylcarbonyl, C₂-C₈ haloalkylcarbonyl, C₄-C₁₀        cycloalkylcarbonyl, C₂-C₈ alkoxycarbonyl, C₂-C₈        haloalkoxycarbonyl, C₂-C₈ alkylaminocarbonyl, C₃-C₁₀        dialkylaminocarbonyl or C₄-C₁₀ cycloalkylaminocarbonyl;    -   R² and R³ are each independently H or C₁-C₄ alkyl;    -   R⁴ and R⁵ are each independently H, halogen, C₁-C₄ alkyl or        C₁-C₄ alkoxy;    -   R⁶ is H, C₁-C₆ alkyl or C₁-C₆ alkoxy;    -   R⁷ is H, halogen, C₁-C₄ alkoxy or C₁-C₄ alkyl;    -   each R⁸ is independently cyano, nitro, —CHO, C₂-C₆ alkenyl,        C₂-C₆ alkynyl, C₂-C₈ alkylcarbonyl, C₂-C₈ haloalkylcarbonyl,        C₂-C₈ alkoxycarbonyl, C₄-C₁₀ cycloalkoxycarbonyl, C₅-C₁₂        cycloalkylalkoxycarbonyl, C₂-C₈ alkylaminocarbonyl, C₃-C₁₀        dialkylaminocarbonyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy or C₂-C₈        alkylcarbonyloxy;    -   R⁹ is H, C₁-C₆ alkyl, C₂-C₈ alkoxyalkyl, C₂-C₈ alkylthioalkyl,        C₂-C₈ alkylsulfinylalkyl, C₂-C₈ alkylsulfonylalkyl, C₂-C₈        alkylcarbonyl, C₄-C₁₀ cycloalkylcarbonyl, C₂-C₈ alkoxycarbonyl        or C₄-C₁₀ cycloalkoxycarbonyl;    -   each R¹⁰ and R¹¹ is halogen, nitro, C₁-C₈ alkyl, C₁-C₈        cyanoalkyl, C₁-C₈ cyanoalkoxy, C₁-C₈ haloalkyl, C₁-C₈        nitroalkyl, C₂-C₈ alkenyl, C₂-C₈ haloalkenyl, C₂-C₈        nitroalkenyl, C₂-C₈ alkoxyalkyl, C₃-C₈ alkoxyalkoxyalkyl, C₂-C₈        haloalkoxyalkyl, C₂-C₈ haloalkoxyhaloalkoxy, C₄-C₁₀        cycloalkylalkyl, C₄-C₁₀ halocycloalkylalkyl, C₅-C₁₂        alkylcycloalkylalkyl, C₅-C₁₂ cycloalkylalkenyl, C₃-C₈        cycloalkyl, C₃-C₈ halocycloalkyl, C₄-C₁₀ alkylcycloalkyl, C₆-C₁₂        cycloalkylcycloalkyl, C₃-C₈ cycloalkenyl, C₃-C₈        halocycloalkenyl, C₂-C₈ haloalkoxyalkoxy, C₂-C₈ alkoxyalkoxy,        C₄-C₁₀ cycloalkoxyalkyl, C₂-C₈ alkylcarbonyl, C₂-C₈        haloalkylcarbonyl, C₄-C₁₀ cycloalkylcarbonyl, —C(═O)OH, C₂-C₈        alkoxycarbonyl, C₂-C₈ haloalkoxycarbonyl, C₄-C₁₀        cycloalkoxycarbonyl, C₅-C₁₂ cycloalkylalkoxycarbonyl, —C(═O)NH₂,        C₁-C₈ alkoxy, C₁-C₈ haloalkoxy, C₂-C₈ alkenyloxy, C₂-C₈        haloalkenyloxy, C₃-C₈ cycloalkoxy, C₃-C₈ halocycloalkoxy, C₄-C₁₀        cycloalkylalkoxy, C₃-C₁₀ alkylcarbonylalkoxy, C₂-C₈        alkylcarbonyloxy, C₂-C₈ haloalkylcarbonyloxy, C₄-C₁₀        cycloalkylcarbonyloxy, C₁-C₈ alkylsulfonyloxy, C₁-C₈        haloalkylsulfonyloxy, C₁-C₈ alkylsulfonyl, C₁-C₈        haloalkylsulfonyl, C₃-C₈ cycloalkylsulfonyl;    -   each G¹ is independently phenyl; or a 6-membered heterocyclic        ring, each substituted or unsubstituted on ring members with up        to 4 substituents independently selected from R¹⁷;    -   each R¹⁶ and R¹⁷ is independently halogen, cyano, hydroxy,        amino, nitro, —CHO, —C(═O)OH, —C(═O)NH₂, —SO₂NH₂, C₁-C₆ alkyl,        C₁-C₆ haloalkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₂-C₈        alkylcarbonyl, C₁-C₈ hydroxyalkyl, C₂-C₈ haloalkylcarbonyl,        C₂-C₆ alkoxyalkyl, C₂-C₆ alkylaminoalkyl, C₂-C₈ alkoxycarbonyl,        C₃-C₈ cycloalkyl, C₄-C₁₀ cycloalkoxycarbonyl, C₅-C₁₂        cycloalkylalkoxycarbonyl, C₂-C₈ alkylaminocarbonyl, C₃-C₁₀        dialkylaminocarbonyl, C₃-C₈ dialkylaminoalkyl, C₁-C₆ alkoxy,        C₁-C₆ haloalkoxy, C₂-C₈ alkylcarbonyloxy or C₁-C₆ alkylthio; and    -   provided the sum of u and v is 2.        Embodiment B. A compound of Embodiment A wherein    -   L is selected from L-1, L-2 or L-3;    -   R^(A) is C₁-C₇ alkyl, C₁-C₇ haloalkyl, C₁-C₇ alkoxy or C₁-C₇        haloalkoxy; each substituted or unsubstituted with up to 2        substituents independently selected from R⁸; or    -   R^(A) is G¹;    -   R^(B) is H, —OCH₃, CF₃ or CH₃;    -   R^(C) is H, C₁-C₂ alkoxy or C₁-C₂ alkyl;    -   R^(D) is H, CH₃, CH₂CH₃ or —C(═O)CH₃ CH₂CH₃;    -   R^(E) is H, hydroxy, amino, cyano, formyl, —C(O)NH₂, C₁-C₆        alkyl, C₃-C₆ cycloalkyl, C₄-C₈ cycloalkylalkyl, C₂-C₈        alkoxyalkyl, C₃-C₈ alkoxyalkoxyalkyl, C₂-C₈ alkylcarbonyl,        C₄-C₁₀ cycloalkylcarbonyl, C₅-C₁₀ cycloalkylcarbonylalkyl, C₂-C₈        alkoxycarbonyl, C₄-C₁₀ cycloalkoxycarbonyl, C₁-C₆ alkylsulfonyl;    -   R^(F) is C₂-C₈ alkylcarbonyl, C₄-C₁₀ cycloalkylcarbonyl, C₂-C₈        alkoxycarbonyl, C₂-C₈ haloalkoxycarbonyl, C₄-C₁₀        cycloalkoxycarbonyl, C₂-C₈ alkylaminocarbonyl, C₃-C₁₀        dialkylaminocarbonyl, C₄-C₁₀ cycloalkylaminocarbonyl, C₁-C₆        alkylsulfonyl, C₁-C₆ haloalkylsulfonyl, C₃-C₈ cycloalkylsulfonyl        or C₁-C₆ alkylaminosulfonyl; or phenyl substituted or        unsubstituted with R¹⁶;    -   R^(G) is formyl, C₂-C₈ alkylcarbonyl, C₂-C₈ alkoxycarbonyl,        C₄-C₁₀ cycloalkoxycarbonyl, C₂-C₈ alkylaminocarbonyl, C₄-C₁₀        cycloalkylaminocarbonyl, C₁-C₆ alkylsulfonyl, C₁-C₆        haloalkylsulfonyl, C₃-C₈ cycloalkylsulfonyl or C₁-C₆        alkylaminosulfonyl;    -   each R⁸ is independently C₂-C₆ alkenyl, C₁-C₆ alkoxy or C₁-C₆        haloalkoxy;    -   J is —CR²R³— or —CR²R³—CR⁴R⁵—;    -   Y¹ and Y² are each independently O;    -   R¹ is H, C₃-C₈ alkylcarbonylalkyl, C₁-C₆ alkyl, C₁-C₆ haloalkyl,        C₂-C₆ cyanoalkyl, C₃-C₆ cycloalkyl, C₄-C₈ cycloalkylalkyl, C₂-C₈        alkoxyalkyl, C₂-C₈ haloalkoxyalkyl, C₂-C₈ alkylcarbonyl, C₂-C₈        haloalkylcarbonyl, C₄-C₁₀ cycloalkylcarbonyl, C₂-C₈        alkoxycarbonyl or C₂-C₈ haloalkoxycarbonyl;    -   Q¹ is a phenyl ring substituted or unsubstituted with up to 4        substituents independently selected from R¹⁰; or a 5- to        6-membered heterocyclic ring, each ring containing ring members        selected from carbon atoms and 1 to 4 heteroatoms independently        selected from up to 2 O, up to 2 S and up to 4 N atoms, each        ring substituted or unsubstituted with up to 4 substituents        independently selected from R¹⁰ on carbon atom ring members and        selected from R¹² on nitrogen atom ring members;    -   Q² is a phenyl ring, substituted or unsubstituted with up to 4        substituents independently selected from R¹¹; or a 5- to        6-membered heterocyclic ring; or an 8- to 10-membered bicyclic        ring system, each ring or ring system containing ring members        selected from carbon atoms and 1 to 4 heteroatoms independently        selected from up to 2 O, up to 2 S and up to 4 N atoms, wherein        up to 2 carbon ring members are independently selected from        C(═O) and C(═S), and the sulfur atom ring members are        independently selected from S(═O)_(u)(═NR¹⁴)_(v), each ring or        ring system substituted or unsubstituted with up to 4        substituents independently selected from R¹¹ on carbon atom ring        members and selected from R¹³ on nitrogen atom ring members;    -   R² and R³ are each independently H or CH₃;    -   R⁴ and R⁵ are each independently H, halogen or C₁-C₄ alkyl;    -   R⁷ is H, F, Cl or CH₃;    -   R⁹ is H, C₁-C₆ alkyl, C₂-C₈ alkoxyalkyl, C₂-C₈ alkylcarbonyl or        C₂-C₈ alkoxycarbonyl;    -   each R¹⁰ and R¹¹ is independently halogen, C₁-C₈ alkyl, C₁-C₈        haloalkyl, C₂-C₈ alkoxyalkyl, C₃-C₈ alkoxyalkoxyalkyl, C₄-C₁₀        cycloalkylalkyl, C₅-C₁₂ alkylcycloalkylalkyl, C₃-C₈ cycloalkyl,        C₃-C₈ halocycloalkyl, C₆-C₁₂ cycloalkylcycloalkyl, C₃-C₈        halocycloalkenyl, C₂-C₈ haloalkoxyalkoxy, C₂-C₈ alkoxyalkoxy,        C₄-C₁₀ cycloalkoxyalkyl, C₂-C₈ alkylcarbonyl, C₂-C₈        haloalkylcarbonyl, C₄-C₁₀ cycloalkylcarbonyl, C₂-C₈        alkoxycarbonyl, C₄-C₁₀ cycloalkoxycarbonyl, C₅-C₁₂        cycloalkylalkoxycarbonyl, C₁-C₈ alkoxy, C₁-C₈ haloalkoxy, C₂-C₈        haloalkenyloxy, C₃-C₈ cycloalkoxy, C₃-C₈ halocycloalkoxy, C₄-C₁₀        cycloalkylalkoxy, C₃-C₁₀ alkylcarbonylalkoxy or C₂-C₈        haloalkylcarbonyloxy;    -   each R¹² and R¹³ is independently C₁-C₃ alkyl, C₃-C₆ cycloalkyl        or C₂-C₃ alkylcarbonyl;    -   each R¹⁴ is independently H;    -   R¹⁵ is H, CH₃, —(C═O)CH₃ or —(C═O)CF₃;    -   each G¹ is independently phenyl substituted or unsubstituted on        ring members with up to 3 substituents independently selected        from R¹⁷; and    -   each R¹⁶ and R¹⁷ is independently halogen, cyano, hydroxy,        amino, nitro, —CHO, —C(═O)OH, —C(═O)NH₂, —SO₂NH₂, C₁-C₆ alkyl or        C₁-C₆ haloalkyl.        Embodiment C. A compound of Embodiment B wherein    -   L is selected from L-1 or L-2;    -   R^(A) is C₁-C₇ alkyl or C₁-C₇ alkoxy; each substituted or        unsubstituted with up to 2 substituents independently selected        from R⁸;    -   R^(B) is H, —OCH₃ or CH₃;    -   R^(C) is H or CH₃;    -   R^(D) is CH₃ or CH₂CH₃;    -   R^(E) is H, C₁-C₆ alkyl, C₃-C₆ cycloalkyl, C₄-C₈        cycloalkylalkyl, C₂-C₈ alkoxyalkyl, C₂-C₈ alkylcarbonyl, C₂-C₈        alkoxycarbonyl, C₄-C₁₀ cycloalkoxycarbonyl, C₁-C₆ alkylsulfonyl;    -   each R⁸ is independently C₁-C₆ alkoxy or C₁-C₆ haloalkoxy;    -   J is —CR²R³—;    -   Y¹ and Y² are each independently O;    -   R¹ is H, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₂-C₆ cyanoalkyl, C₃-C₆        cycloalkyl, C₄-C₈ cycloalkylalkyl, C₂-C₈ alkoxyalkyl, C₂-C₈        haloalkoxyalkyl or C₂-C₈ alkoxycarbonyl;    -   Q¹ is a phenyl ring substituted or unsubstituted with up to 4        substituents independently selected from R¹⁰;    -   Q² is a phenyl ring, substituted or unsubstituted with up to 4        substituents independently selected from R¹¹; or a 5- to        6-membered heterocyclic ring containing ring members selected        from carbon atoms and 1 to 4 heteroatoms independently selected        from up to 4 N atoms, wherein up to 2 carbon ring members are        independently selected from C(═O) and C(═S), each ring or ring        system substituted or unsubstituted with up to 4 substituents        independently selected from R¹¹ on carbon atom ring members and        selected from R¹³ on nitrogen atom ring members;    -   R² and R³ are each independently H;    -   R⁷ is H or CH₃;    -   R⁹ is H, C₁-C₆ alkyl or C₂-C₈ alkoxycarbonyl;    -   each R¹⁰ and R¹¹ is independently halogen, C₁-C₈ alkyl, C₁-C₈        haloalkyl, C₂-C₈ alkoxyalkyl, C₄-C₁₀ cycloalkylalkyl, C₅-C₁₂        alkylcycloalkylalkyl, C₃-C₈ cycloalkyl, C₃-C₈ halocycloalkyl,        C₂-C₈ haloalkoxyalkoxy, C₁-C₈ alkoxy, C₁-C₈ haloalkoxy or C₂-C₈        alkoxyalkoxy; and    -   each R¹² and R¹³ is independently C₁-C₃ alkyl or C₂-C₃        alkylcarbonyl.        Embodiment D. A compound of Embodiment C wherein    -   L is selected from L-1;    -   R^(A) is C₁-C₃ alkyl substituted or unsubstituted with up to 2        substituents independently selected from R⁸;    -   each R⁸ is independently C₁-C₆ alkoxy;    -   R¹ is H, C₁-C₆ alkyl, C₃-C₆ cycloalkyl, C₄-C₈ cycloalkylalkyl or        C₂-C₈ alkoxyalkyl;    -   Q¹ is a phenyl ring substituted or unsubstituted with up to 3        substituents independently selected from R¹⁰;    -   Q² is a phenyl ring, substituted or unsubstituted with up to 4        substituents independently selected from R¹¹;    -   R⁷ is H;    -   R⁹ is H, CH₃ or —C(═O)CH₃; and    -   each R¹⁰ and R¹¹ is independently halogen, C₁-C₈ alkyl, C₁-C₈        haloalkyl, C₃-C₈ cycloalkyl, C₁-C₈ alkoxy or C₁-C₈ haloalkoxy.        Embodiment E. A compound of Embodiment C wherein    -   L is selected from L-1;    -   R^(A) is C₁-C₃ alkoxy, substituted or unsubstituted with up to 2        substituents independently selected from R⁸;    -   each R⁸ is independently C₁-C₆ alkoxy;    -   R¹ is H, CH₃, CH₂CH₃, cyclopropyl, cyclopropylmethyl or CH₂OCH₃;    -   Q¹ is a phenyl ring substituted or unsubstituted with up to 2        substituents independently selected from R¹⁰;    -   Q² is a phenyl ring, substituted or unsubstituted with up to 3        substituents independently selected from R¹¹;    -   R⁷ is H;    -   R⁹ is H; and    -   each R¹⁰ and R¹¹ is independently halogen, C₁-C₈ alkyl, C₁-C₈        haloalkyl, C₁-C₈ alkoxy or C₁-C₈ haloalkoxy.

Specific Embodiments of the Invention include a compound of the Summaryof the Invention selected from:

-   (3S,4R)—N-(2,3-difluorophenyl)-3-(hydroxymethyl)-1-methyl-2-oxo-4-[4-(trifluoromethyl)-3-pyrrolidinecarboxamide    (cis);-   (3R,4S)—N-(2,3-difluorophenyl)-3-(hydroxymethyl)-1-methyl-2-oxo-4-[4-(trifluoromethyl)-3-pyrrolidinecarboxamide    (trans);-   (3S,4R)-3-[(acetyloxy)methyl]-N-(2,3-difluorophenyl)-1-methyl-2-oxo-4-[4-(trifluoromethyl)-3-pyrrolidinenecarboxamide;    and-   (3S,4R)-3-acetyl-N-(2,3-difluorophenyl)-1-methyl-2-oxo-4-[4-(trifluoromethyl)-3-pyrrolidinecarboxamide.

This invention also relates to a method for controlling undesiredvegetation comprising applying to the locus of the vegetationherbicidally effective amounts of the compounds of the invention (e.g.,as a composition described herein). Of note as embodiments relating tomethods of use are those involving the compounds of embodimentsdescribed above. Compounds of the invention are particularly useful forselective control of weeds in crops such as wheat, barley, maize,soybean, sunflower, cotton, oilseed rape and rice, and specialty cropssuch as sugarcane, citrus, fruit and nut crops.

Also noteworthy as embodiments are herbicidal compositions of thepresent invention comprising the compounds of embodiments describedabove.

This invention also includes a herbicidal mixture comprising (a) acompound selected from Formula 1, N-oxides, and salts thereof, and (b)at least one additional active ingredient selected from (b1) photosystemII inhibitors, (b2) acetohydroxy acid synthase (AHAS) inhibitors, (b3)acetyl-CoA carboxylase (ACCase) inhibitors, (b4) auxin mimics, (b5)5-enol-pyruvylshikimate-3-phosphate (EPSP) synthase inhibitors, (b6)photosystem I electron diverters, (b7) protoporphyrinogen oxidase (PPO)inhibitors, (b8) glutamine synthetase (GS) inhibitors, (b9) very longchain fatty acid (VLCFA) elongase inhibitors, (b10) auxin transportinhibitors, (b11) phytoene desaturase (PDS) inhibitors, (b12)4-hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitors, (b13)homogentisate solenesyltransererase (HST) inhibitors, (b14) cellulosebiosynthesis inhibitors, (b15) other herbicides including mitoticdisruptors, organic arsenicals, asulam, bromobutide, cinmethylin,cumyluron, dazomet,2-[(2,5-dichlorophenyl)methyl]-4,4-dimethyl-3-isoxazolidinone,difenzoquat, dymron, etobenzanid, flurenol, fosamine, fosamine-ammonium,hydantocidin, metam, methyldymron, oleic acid, oxaziclomefone,pelargonic acid and pyributicarb, and (b16) herbicide safeners; andsalts of compounds of (b1) through (b16).

“Photosystem II inhibitors” (b1) are chemical compounds that bind to theD-1 protein at the Q_(B)-binding niche and thus block electron transportfrom Q_(A) to Q_(B) in the chloroplast thylakoid membranes. Theelectrons blocked from passing through photosystem II are transferredthrough a series of reactions to form toxic compounds that disrupt cellmembranes and cause chloroplast swelling, membrane leakage, andultimately cellular destruction. The Q_(B)-binding niche has threedifferent binding sites: binding site A binds the triazines such asatrazine, triazinones such as hexazinone, and uracils such as bromacil,binding site B binds the phenylureas such as diuron, and binding site Cbinds benzothiadiazoles such as bentazon, nitriles such as bromoxyniland phenyl-pyridazines such as pyridate. Examples of photosystem IIinhibitors include ametryn, amicarbazone, atrazine, bentazon, bromacil,bromofenoxim, bromoxynil, chlorbromuron, chloridazon, chlorotoluron,chloroxuron, cumyluron, cyanazine, daimuron, desmedipham, desmetryn,dimefuron, dimethametryn, diuron, ethidimuron, fenuron, fluometuron,hexazinone, ioxynil, isoproturon, isouron, lenacil, linuron, metamitron,methabenzthiazuron, metobromuron, metoxuron, metribuzin, monolinuron,neburon, pentanochlor, phenmedipham, prometon, prometryn, propanil,propazine, pyridafol, pyridate, siduron, simazine, simetryn,tebuthiuron, terbacil, terbumeton, terbuthylazine, terbutryn andtrietazine.

“AHAS inhibitors” (b2) are chemical compounds that inhibit acetohydroxyacid synthase (AHAS), also known as acetolactate synthase (ALS), andthus kill plants by inhibiting the production of the branched-chainaliphatic amino acids such as valine, leucine and isoleucine, which arerequired for protein synthesis and cell growth. Examples of AHASinhibitors include amidosulfuron, azimsulfuron, bensulfuron-methyl,bispyribac-sodium, cloransulam-methyl, chlorimuron-ethyl, chlorsulfuron,cinosulfuron, cyclosulfamuron, diclosulam, ethametsulfuron-methyl,ethoxysulfuron, flazasulfuron, florasulam, flucarbazone-sodium,flumetsulam, flupyrsulfuron-methyl, flupyrsulfuron-sodium,foramsulfuron, halosulfuron-methyl, imazamethabenz-methyl, imazamox,imazapic, imazapyr, imazaquin, imazethapyr, imazosulfuron,iodosulfuron-methyl (including sodium salt), iofensulfuron(2-iodo-N-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino]carbonyl]benzenesulfonamide),mesosulfuron-methyl, metazosulfuron(3-chloro-4-(5,6-dihydro-5-methyl-1,4,2-dioxazin-3-yl)-N-[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]-1-methyl-1H-pyrazole-5-sulfonamide),metosulam, metsulfuron-methyl, nicosulfuron, oxasulfuron, penoxsulam,primisulfuron-methyl, propoxycarbazone-sodium, propyrisulfuron(2-chloro-N-[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]-6-propylimidazo[1,2-b]pyridazine-3-sulfonamide),prosulfuron, pyrazosulfuron-ethyl, pyribenzoxim, pyriftalid,pyriminobac-methyl, pyrithiobac-sodium, rimsulfuron,sulfometuron-methyl, sulfosulfuron, thiencarbazone,thifensulfuron-methyl, triafamone(N-[2-[(4,6-dimethoxy-1,3,5-triazin-2-yl)carbonyl]-6-fluorophenyl]-1,1-difluoro-N-methylmethanesulfonamide),triasulfuron, tribenuron-methyl, trifloxysulfuron (including sodiumsalt), triflusulfuron-methyl and tritosulfuron.

“ACCase inhibitors” (b3) are chemical compounds that inhibit theacetyl-CoA carboxylase enzyme, which is responsible for catalyzing anearly step in lipid and fatty acid synthesis in plants. Lipids areessential components of cell membranes, and without them, new cellscannot be produced. The inhibition of acetyl CoA carboxylase and thesubsequent lack of lipid production leads to losses in cell membraneintegrity, especially in regions of active growth such as meristems.Eventually shoot and rhizome growth ceases, and shoot meristems andrhizome buds begin to die back. Examples of ACCase inhibitors includealloxydim, butroxydim, clethodim, clodinafop, cycloxydim, cyhalofop,diclofop, fenoxaprop, fluazifop, haloxyfop, pinoxaden, profoxydim,propaquizafop, quizalofop, sethoxydim, tepraloxydim and tralkoxydim,including resolved forms such as fenoxaprop-P, fluazifop-P, haloxyfop-Pand quizalofop-P and ester forms such as clodinafop-propargyl,cyhalofop-butyl, diclofop-methyl and fenoxaprop-P-ethyl.

Auxin is a plant hormone that regulates growth in many plant tissues.“Auxin mimics” (b4) are chemical compounds mimicking the plant growthhormone auxin, thus causing uncontrolled and disorganized growth leadingto plant death in susceptible species. Examples of auxin mimics includeaminocyclopyrachlor(6-amino-5-chloro-2-cyclopropyl-4-pyrimidinecarboxylic acid) and itsmethyl and ethyl esters and its sodium and potassium salts,aminopyralid, benazolin-ethyl, chloramben, clacyfos, clomeprop,clopyralid, dicamba, 2,4-D, 2,4-DB, dichlorprop, fluroxypyr, halauxifen(4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-2-pyridinecarboxylicacid), halauxifen-methyl (methyl4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-2-pyridinecarboxylate),MCPA, MCPB, mecoprop, picloram, quinclorac, quinmerac, 2,3,6-TBA,triclopyr, and methyl4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoro-2-pyridinecarboxylate.

“EPSP synthase inhibitors” (b5) are chemical compounds that inhibit theenzyme, 5-enol-pyruvylshikimate-3-phosphate synthase, which is involvedin the synthesis of aromatic amino acids such as tyrosine, tryptophanand phenylalanine. EPSP inhibitor herbicides are readily absorbedthrough plant foliage and translocated in the phloem to the growingpoints. Glyphosate is a relatively nonselective postemergence herbicidethat belongs to this group. Glyphosate includes esters and salts such asammonium, isopropylammonium, potassium, sodium (including sesquisodium)and trimesium (alternatively named sulfosate).

“Photosystem I electron diverters” (b6) are chemical compounds thataccept electrons from Photosystem I, and after several cycles, generatehydroxyl radicals. These radicals are extremely reactive and readilydestroy unsaturated lipids, including membrane fatty acids andchlorophyll. This destroys cell membrane integrity, so that cells andorganelles “leak”, leading to rapid leaf wilting and desiccation, andeventually to plant death. Examples of this second type ofphotosynthesis inhibitor include diquat and paraquat.

“PPO inhibitors” (b7) are chemical compounds that inhibit the enzymeprotoporphyrinogen oxidase, quickly resulting in formation of highlyreactive compounds in plants that rupture cell membranes, causing cellfluids to leak out. Examples of PPO inhibitors includeacifluorfen-sodium, azafenidin, benzfendizone, bifenox, butafenacil,carfentrazone, carfentrazone-ethyl, chlomethoxyfen, cinidon-ethyl,cyclopyranil, fluazolate, flufenpyr-ethyl, flumiclorac-pentyl,flumioxazin, fluoroglycofen-ethyl, fluthiacet-methyl, fomesafen,halosafen, lactofen, oxadiargyl, oxadiazon, oxyfluorfen, pentoxazone,profluazol, pyraclonil, pyraflufen-ethyl, saflufenacil, sulfentrazone,thidiazimin, trifludimoxazin(dihydro-1,5-dimehyl-6-thioxo-3-[2,2,7-trifluoro-3,4-dihydro-3-oxo-4-(2-propyn-1-yl)-2H-1,4-benzoxazin-6-yl]-1,3,5-triazine-2,4(1H,3H)-dione)and tiafenacil (methylN-[2-[[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl]thio]-1-oxopropyl]-β-alaninate).

“GS inhibitors” (b8) are chemical compounds that inhibit the activity ofthe glutamine synthetase enzyme, which plants use to convert ammoniainto glutamine. Consequently, ammonia accumulates and glutamine levelsdecrease. Plant damage probably occurs due to the combined effects ofammonia toxicity and deficiency of amino acids required for othermetabolic processes. The GS inhibitors include glufosinate and itsesters and salts such as glufosinate-ammonium and other phosphinothricinderivatives, glufosinate-P((2S)-2-amino-4-(hydroxymethylphosphinyl)butanoic acid) and bilanaphos.

“VLCFA elongase inhibitors” (b9) are herbicides having a wide variety ofchemical structures, which inhibit the elongase. Elongase is one of theenzymes located in or near chloroplasts which are involved inbiosynthesis of VLCFAs. In plants, very-long-chain fatty acids are themain constituents of hydrophobic polymers that prevent desiccation atthe leaf surface and provide stability to pollen grains. Such herbicidesinclude acetochlor, alachlor, anilofos, butachlor, cafenstrole,dimethachlor, dimethenamid, diphenamid, fenoxasulfone(3-[[(2,5-dichloro-4-ethoxyphenyl)methyl]sulfonyl]-4,5-dihydro-5,5-dimethylisoxazole),fentrazamide, flufenacet, indanofan, mefenacet, metazachlor,metolachlor, naproanilide, napropamide, napropamide-M((2R)—N,N-diethyl-2-(1-naphthalenyloxy)propanamide), pethoxamid,piperophos, pretilachlor, propachlor, propisochlor, pyroxasulfone, andthenylchlor, including resolved forms such as S-metolachlor andchloroacetamides and oxyacetamides.

“Auxin transport inhibitors” (b10) are chemical substances that inhibitauxin transport in plants, such as by binding with an auxin-carrierprotein. Examples of auxin transport inhibitors include diflufenzopyr,naptalam (also known as N-(1-naphthyl)phthalamic acid and2-[(1-naphthalenylamino)carbonyl]benzoic acid).

“PDS inhibitors” (b11) are chemical compounds that inhibit carotenoidbiosynthesis pathway at the phytoene desaturase step. Examples of PDSinhibitors include beflubutamid, S-beflubutamid, diflufenican,fluridone, flurochloridone, flurtamone norflurzon and picolinafen.

“HPPD inhibitors” (b12) are chemical substances that inhibit thebiosynthesis of synthesis of 4-hydroxyphenyl-pyruvate dioxygenase.Examples of HPPD inhibitors include benzobicyclon, benzofenap,bicyclopyrone(4-hydroxy-3-[[2-[(2-methoxyethoxy)methyl]-6-(trifluoromethyl)-3-pyridinyl]carbonyl]bicyclo[3.2.1]oct-3-en-2-one),fenquinotrione(2-[[8-chloro-3,4-dihydro-4-(4-methoxyphenyl)-3-oxo-2-quinoxalinyl]carbonyl]-1,3-cyclohexanedione),isoxachlortole, isoxaflutole, mesotrione, pyrasulfotole, pyrazolynate,pyrazoxyfen, sulcotrione, tefuryltrione, tembotrione, tolpyralate(1-[[1-ethyl-4-[3-(2-methoxyethoxy)-2-methyl-4-(methylsulfonyl)benzoyl]-1H-pyrazol-5-yl]oxy]ethylmethyl carbonate), topramezone,5-chloro-3-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-1-(4-methoxyphenyl)-2(1H)-quinoxalinone,4-(2,6-diethyl-4-methylphenyl)-5-hydroxy-2,6-dimethyl-3(2H)-pyridazinone,4-(4-fluorophenyl)-6-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-2-methyl-1,2,4-triazine-3,5(2H,4H)-dione,5-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-2-(3-methoxyphenyl)-3-(3-methoxypropyl)-4(3H)-pyrimidinone,2-methyl-N-(4-methyl-1,2,5-oxadiazol-3-yl)-3-(methylsulfinyl)-4-(trifluoromethyl)benzamideand2-methyl-3-(methylsulfonyl)-N-(1-methyl-1H-tetrazol-5-yl)-4-(trifluoromethyl)benzamide.

“HST inhibitors” (b13) disrupt a plant's ability to converthomogentisate to 2-methyl-6-solanyl-1,4-benzoquinone, thereby disruptingcarotenoid biosynthesis. Examples of HST inhibitors include haloxydine,pyriclor,3-(2-chloro-3,6-difluorophenyl)-4-hydroxy-1-methyl-1,5-naphthyridin-2(1H)-one,7-(3,5-dichloro-4-pyridinyl)-5-(2,2-difluoroethyl)-8-hydroxypyrido[2,3-b]pyrazin-6(5H)-oneand4-(2,6-diethyl-4-methylphenyl)-5-hydroxy-2,6-dimethyl-3(2H)-pyridazinone.

HST inhibitors also include compounds of Formulae A and B.

-   wherein R^(d1) is H, Cl or CF₃; R^(d2) is H, Cl or Br; R^(d3) is H    or Cl; R^(d4) is H, Cl or CF₃; R^(d5) is CH₃, CH₂CH₃ or CH₂CHF₂; and    R^(d6) is OH, or —OC(═O)-i-Pr; and R^(e1) is H, F, Cl, CH₃ or    CH₂CH₃; R^(e2) is H or CF₃; R^(e3) is H, CH₃ or CH₂CH₃; R^(e4) is H,    F or Br; R^(e5) is Cl, CH₃, CF₃, OCF₃ or CH₂CH₃; R^(e6) is H, CH₃,    CH₂CHF₂ or C≡CH; R^(e7) is OH, —OC(═O)Et, —OC(═O)-i-Pr or    —OC(═O)-t-Bu; and A^(e8) is N or CH.

“Cellulose biosynthesis inhibitors” (b14) inhibit the biosynthesis ofcellulose in certain plants. They are most effective when appliedpreemergence or early postemergence on young or rapidly growing plants.Examples of cellulose biosynthesis inhibitors include chlorthiamid,dichlobenil, flupoxam, indaziflam(N²-[(1R,2S)-2,3-dihydro-2,6-dimethyl-1H-inden-1-yl]-6-(1-fluoroethyl)-1,3,5-triazine-2,4-diamine),isoxaben and triaziflam.

“Other herbicides” (b15) include herbicides that act through a varietyof different modes of action such as mitotic disruptors (e.g.,flamprop-M-methyl and flamprop-M-isopropyl), organic arsenicals (e.g.,DSMA, and MSMA), 7,8-dihydropteroate synthase inhibitors, chloroplastisoprenoid synthesis inhibitors and cell-wall biosynthesis inhibitors.Other herbicides include those herbicides having unknown modes of actionor do not fall into a specific category listed in (b1) through (b14) oract through a combination of modes of action listed above. Examples ofother herbicides include aclonifen, asulam, amitrole, bromobutide,cinmethylin, clomazone, cumyluron, cyclopyrimorate(6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl4-morpholinecarboxylate), daimuron,2-[(2,5-dichlorophenyl)methyl]-4,4-dimethyl-3-isoxazolidinone,difenzoquat, etobenzanid, fluometuron, flurenol, fosamine,fosamine-ammonium, dazomet, dymron, ipfencarbazone(1-(2,4-dichlorophenyl)-N-(2,4-difluorophenyl)-1,5-dihydro-N-(1-methylethyl)-5-oxo-4H-1,2,4-triazole-4-carboxamide),metam, methyldymron, oleic acid, oxaziclomefone, pelargonic acid,pyributicarb and5-[[(2,6-difluorophenyl)methoxy]methyl]-4,5-dihydro-5-methyl-3-(3-methyl-2-thienyl)isoxazole.“Other herbicides” (b15) also include a compound of Formula (b15A),

wherein R¹ is Cl, Br or CN; and R² is C(═O)CH₂CH₂CF₃, CH₂CH₂CH₂CH₂CF₃ or3-CHF₂-isoxazol-5-yl. “Other herbicides” (b15) also include a compoundof Formula (b15B)

wherein R¹ is CH₃, R² is Me, R⁴ is OCHF₂, G is H, and n is 0; R¹ is CH₃,R² is Me, R³ is 5-F, R⁴ is Cl, G is H, and n is 1; R¹ is CH₃, R² is Cl,R⁴ is Me, G is H, and n is 0; R¹ is CH₃, R² is Me, R⁴ is Cl, G is H, andn is 0; R¹ is CH₃, R² is Me, R³ is 5-Me, R⁴ is OCHF₂, G is H, and n is1; R¹ is CH₃, R² is Me, R³ is 5-Br, R⁴ is OCHF₂, G is H, and n is 1; R¹is CH₃, R² is Me, R³ is 5-Cl, R⁴ is Cl, G is H, and n is 1; or R¹ isCH₃, R² is CH₃, R⁴ is OCHF₂, G is C(O)Me, and n is 0.

“Other herbicides” (b15) also include a compound of Formula (b15C)

wherein

R¹ is CH₃, R² is Cl, and G is H; or

R¹ is CH₃, R² is Cl, and G is C(O)Me.

“Herbicide safeners” (b16) are substances added to a herbicideformulation to eliminate or reduce phytotoxic effects of the herbicideto certain crops. These compounds protect crops from injury byherbicides but typically do not prevent the herbicide from controllingundesired vegetation. Examples of herbicide safeners include but are notlimited to benoxacor, cloquintocet-mexyl, cumyluron, cyometrinil,cyprosulfamide, daimuron, dichlormid, dicyclonon, dietholate,dimepiperate, fenchlorazole-ethyl, fenclorim, flurazole, fluxofenim,furilazole, isoxadifen-ethyl, mefenpyr-diethyl, mephenate,methoxyphenone, naphthalic anhydride, oxabetrinil,N-(aminocarbonyl)-2-methylbenzenesulfonamide andN-(aminocarbonyl)-2-fluorobenzenesulfonamide,1-bromo-4-[(chloromethyl)sulfonyl]benzene,2-(dichloromethyl)-2-methyl-1,3-dioxolane (MG 191),4-(dichloroacetyl)-1-oxa-4-azospiro[4.5]decane (MON 4660),2,2-dichloro-1-(2,2,5-trimethyl-3-oxazolidinyl)-ethanone and2-methoxy-N-[[4-[[(methylamino)carbonyl]amino]phenyl]sulfonyl]-benzamide.

The compounds of Formula 1 can be prepared by general methods known inthe art of synthetic organic chemistry. Of note are the followingmethods described in Schemes 1-5 and variations thereof. The definitionsof R¹, R⁷, R⁹, Q¹, Q², Y¹, Y², J and W in the compounds of Formulae 1through 2 below are as defined above in the Summary of the Inventionunless otherwise noted. Formulae 1A-1F are various subsets of a compoundof Formula 1. Substituents for each subset Formula are as defined forits parent Formula unless otherwise noted.

A Compound of Formula 1 can be prepared by reaction of a compound ofFormula 2 with an electrophile as shown in Scheme 1. The addition andsubstitution reactions are carried out in the presence of astoichiometric, superstoichiometric, or catalytic amount of base andtypically in the presence of a co-solvent. Suitable bases for thereaction include, but are not limited to, sodium hydride, sodiummethoxide, sodium ethoxide, cesium carbonate, potassium carbonate,potassium tert-butoxide, lithium diisopropylamide, lithiumbis(trimethylsilyl)amide, sodium bis(trimethylsilyl)amide, potassiumbis(trimethylsilyl)amide, pyridine, triethylamine, andN,N-diisopropylethylamine. Suitable electrophiles for the reactioninclude, but are not limited to acyl chlorides, acyl anhydrides,chloroformates, cyanoformates, isocyanates, aldehydes, ketones, imines,iminium halides, electron-deficient alkenes (such as acrylates,acrylamides, acrylonitriles, vinylketones, and vinylsulfones),alkylhalides, and alkylsulfonates. Typically the reaction is conductedin a solvent such as water, methanol, ethanol, tetrahydrofuran,dimethylsulfoxide, N,N-dimethylformamide, N,N-dimethylacetamide,N-methylpyrrolidinone and acetonitrile or a mixture thereof attemperatures ranging from −78° C. to the reflux temperature of thesolvent. The method of Scheme 1 for the preparation of compounds ofFormula 1 wherein L is L-1 utilizing lithium bis(trimethylsilyl)amideand acetyl chloride is illustrated by Step A of Synthesis Example 3. Themethod of Scheme 1 for the preparation of compounds of Formula 1 whereinL is L-3 utilizing a catalytic amount of potassium hydroxide andparaformaldehyde is illustrated by Step A of Synthesis Example 1.

A compound of Formula 1B (i.e. a compound of Formula 1 wherein L is L-3and R^(F) is other than H) can be prepared by reaction of an alcohol ofFormula 1A (i.e. a compound of Formula 1 wherein L is L-3 and R^(F) isH) with an electrophile as shown in Scheme 2. The reactions are carriedout in the presence of a suitable base and typically in the presence ofa co-solvent. Suitable bases for the reaction include, but are notlimited to, sodium hydride, sodium methoxide, sodium ethoxide, cesiumcarbonate, potassium carbonate, potassium tert-butoxide, lithiumdiisopropylamide, lithium bis(trimethylsilyl)amide, sodiumbis(trimethylsilyl)amide, potassium bis(trimethylsilyl)amide, pyridine,triethylamine, and N,N-diisopropylethylamine. Suitable electrophiles forthe reaction include, but are not limited to acyl chlorides, acylanhydrides, chloroformates, cyanoformates, isocyanates, sulfonylchlorides, sulfinyl chlorides, and phosphoryl chlorides. Typically thereaction is conducted in a solvent such as water, methanol, ethanol,tetrahydrofuran, dimethylsulfoxide, N,N-dimethylformamide,N,N-dimethylacetamide, N-methylpyrrolidinone and acetonitrile or amixture thereof at temperatures ranging from −78° C. to the refluxtemperature of the solvent. The method of Scheme 2 for the preparationof compounds of Formula 1A wherein L is L-3 utilizing pyridine andacetyl chloride is illustrated by Step A of Synthesis Example 2.

A compound of Formula 1D (i.e. a compound of Formula 1 wherein L is L-2and R^(D) is other than H) can be prepared by reaction of compounds ofFormula 1C (i.e. a compound of Formula 1 wherein L is L-2 and R^(D) isH) with an electrophile as shown in Scheme 3. The reactions are carriedout in the presence of a suitable base and typically in the presence ofa co-solvent. Suitable bases for the reaction include, but are notlimited to, sodium hydride, sodium methoxide, sodium ethoxide, cesiumcarbonate, potassium carbonate, potassium tert-butoxide, lithiumdiisopropylamide, lithium bis(trimethylsilyl)amide, sodiumbis(trimethylsilyl)amide, potassium bis(trimethylsilyl)amide, pyridine,triethylamine, and N,N-diisopropylethylamine. Suitable electrophiles forthe reaction include, but are not limited to acyl chlorides, acylanhydrides, chloroformates, cyanoformates, isocyanates,electron-deficient alkenes (such as acrylates, acrylamides,acrylonitriles, vinylketones, and vinylsulfones), alkylhalides,alkylsulfonates, sulfonyl chlorides, sulfinyl chlorides, and phosphorylchlorides. Typically the reaction is conducted in a solvent such aswater, methanol, ethanol, tetrahydrofuran, dimethylsulfoxide,N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidinone andacetonitrile or a mixture thereof at temperatures ranging from −78° C.to the reflux temperature of the solvent.

A compound of Formula 1E (i.e. a compound of Formula 1 wherein L is L-3and R^(F) is C(═O)R where the atom bonded to the carbonyl is carbon) canalso be prepared by reaction of carboxylic acids with an alcohol ofFormula 1A (i.e. a compound of Formula 1 wherein L is L-3 and R^(F) isH) in the presence of a dehydrative coupling reagent such aspropylphosphonic anhydride, dicyclohexylcarbodiimide,N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide,N,N′-carbonyldiimidazole, 2-chloro-1,3-dimethylimidazolium chloride or2-chloro-1-methylpyridinium iodide, optionally in the presence of acatalyst such as N,N-dimethyl-4-aminopyridine as shown in Scheme 4.Polymer-supported reagents, such as polymer-supportedcyclohexylcarbodiimide, are also suitable. These reactions are typicallyrun at temperatures ranging from 0° C. to the boiling point of thesolvent in a solvent such as dichloromethane, acetonitrile,N,N-dimethylformamide or ethyl acetate in the presence of a base such astriethylamine, N,N-diisopropylamine, or1,8-diazabicyclo[5.4.0]undec-7-ene.

A compound of Formula 1F (i.e. a compound of Formula 1 wherein L is L-2and R^(D) is C(O)R where the atom bonded to the carbonyl is carbon) canalso be prepared by reaction of carboxylic acids with a compound ofFormula 1C (i.e. a compound of Formula 1 wherein L is L-2 and R^(D) isH) in the presence of a dehydrative coupling reagent such aspropylphosphonic anhydride, dicyclohexylcarbodiimide,N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide,N,N′-carbonyldiimidazole, 2-chloro-1,3-dimethylimidazolium chloride or2-chloro-1-methylpyridinium iodide as shown in Scheme 5.Polymer-supported reagents, such as polymer-supportedcyclohexylcarbodiimide, are also suitable. These reactions are typicallyrun at temperatures ranging from 0 to 60° C. in a solvent such asdichloromethane, acetonitrile, N,N-dimethylformamide or ethyl acetate inthe presence of a base such as triethylamine, N,N-diisopropylamine, or1,8-diazabicyclo[5.4.0]undec-7-ene. See Organic Process Research &Development 2009, 13, 900-906 for coupling conditions employingpropylphosphonic anhydride.

It is recognized by one skilled in the art that various functionalgroups can be converted into others to provide different compounds ofFormula 1. For a valuable resource that illustrates the interconversionof functional groups in a simple and straightforward fashion, seeLarock, R. C., Comprehensive Organic Transformations: A Guide toFunctional Group Preparations, 2nd Ed., Wiley-VCH, New York, 1999. Forexample, intermediates for the preparation of compounds of Formula 1 maycontain aromatic nitro groups, which can be reduced to amino groups, andthen be converted via reactions well known in the art such as theSandmeyer reaction, to various halides, providing compounds ofFormula 1. The above reactions can also in many cases be performed inalternate order It is recognized that some reagents and reactionconditions described above for preparing compounds of Formula 1 may notbe compatible with certain functionalities present in the intermediates.In these instances, the incorporation of protection/deprotectionsequences or functional group interconversions into the synthesis willaid in obtaining the desired products.

The use and choice of the protecting groups will be apparent to oneskilled in chemical synthesis (see, for example, Greene, T. W.; Wuts, P.G. M. Protective Groups in Organic Synthesis, 2nd ed.; Wiley: New York,1991). One skilled in the art will recognize that, in some cases, afterthe introduction of a given reagent as depicted in any individualscheme, it may be necessary to perform additional routine syntheticsteps not described in detail to complete the synthesis of compounds ofFormula 1. One skilled in the art will also recognize that it may benecessary to perform a combination of the steps illustrated in the aboveschemes in an order other than that implied by the particular presentedto prepare the compounds of Formula 1.

One skilled in the art will also recognize that compounds of Formula 1and the intermediates described herein can be subjected to variouselectrophilic, nucleophilic, radical, organometallic, oxidation, andreduction reactions to add substituents or modify existing substituents.

Without further elaboration, it is believed that one skilled in the artusing the preceding description can utilize the present invention to itsfullest extent. The following non-limiting Examples are illustrative ofthe invention. Steps in the following Examples illustrate a procedurefor each step in an overall synthetic transformation, and the startingmaterial for each step may not have necessarily been prepared by aparticular preparative run whose procedure is described in otherExamples or Steps. Percentages are by weight except for chromatographicsolvent mixtures or where otherwise indicated. Parts and percentages forchromatographic solvent mixtures are by volume unless otherwiseindicated. ¹H NMR spectra are reported in ppm downfield fromtetramethylsilane in CDCl₃ at 500 Mhz unless otherwise noted; “s” meanssinglet, “d” means doublet, “t” means triplet, “q” means quartet, “m”means multiplet, “dd” means doublet of doublets, “dt” means doublet oftriplets, and “br s” means broad singlet.

Synthesis Example 1 Preparation of(3S,4R)—N-(2,3-difluorophenyl)-3-(hydroxymethyl)-1-methyl-2-oxo-4-[4-(trifluoromethyl)phenyl]-3-pyrrolidinecarboxamide(Compounds 4 and 5) Step A: Preparation of(3S,4R)—N-(2,3-difluorophenyl)-3-(hydroxymethyl)-1-methyl-2-oxo-4-[4-(trifluoromethyl)phenyl]-3-pyrrolidinecarboxamide

A solution of(3S,4S)—N-(2,3-difluorophenyl)-1-methyl-2-oxo-4-[4-(trifluoromethyl)phenyl]-3-pyrrolidinecarboxamide(0.80 g, 2.0 mmol), paraformaldehyde (0.072 g, 2.4 mmol) and potassiumhydroxide (0.002 g, 0.04 mmol) were added to tetrahydrofuran (16 mL) andheated to the reflux temperature of the solvent for 30 min. The reactionmixture was concentrated to afford the crude product. The crude productwas purified by column chromatography, eluting with 0% to 100% ethylacetate in hexanes, to afford the title compound, a compound of thepresent invention, as a colorless oil (0.20 g) and its diastereomer((3R,4R)—N-(2,3-difluorophenyl)-3-(hydroxymethyl)-1-methyl-2-oxo-4-[4-(trifluoromethyl)phenyl]-3-pyrrolidinecarboxamide),a compound of the present invention, as a colorless solid (0.60 g).

¹H NMR δ 10.22 (br s, 1H), 7.52 (d, J=8.2 Hz, 2H), 7.50-7.45 (m, 1H),7.33 (d, J=8.2 Hz, 2H), 6.99-6.82 (m, 2H), 4.18-4.08 (m, 1H), 4.07-4.00(m, 1H), 3.98-3.83 (m, 2H), 3.56-3.48 (m, 1H), 3.15-3.11 (m, 1H), 3.07(s, 3H).

diastereomer: ¹H NMR δ 10.27 (br s, 1H), 8.03-7.97 (m, 1H), 7.72 (d,J=8.4 Hz, 2H), 7.64 (d, J=8.4 Hz, 2H), 7.08-6.99 (m, 1H), 6.95-6.86 (m,1H), 4.40-4.33 (m, 1H), 3.91-3.64 (m, 4H), 3.08 (s, 3H), 2.24-2.20 (m,1H).

Synthesis Example 2 Preparation of(3S,4R)-3-[(acetyloxy)methyl]-N-(2,3-difluorophenyl)-1-methyl-2-oxo-4-[4-(trifluoromethyl)phenyl]-3-pyrrolidincarboxamide(Compound 2) Step A: Preparation of(3S,4R)-3-[(acetyloxy)methyl]-N-(2,3-difluorophenyl)-1-methyl-2-oxo-4-[4-(trifluoromethyl)phenyl]-3-pyrrolidincarboxamide

(3S,4R)—N-(2,3-difluorophenyl)-3-(hydroxymethyl)-1-methyl-2-oxo-4-[4-(trifluoromethyl)phenyl]-3-pyrrolidinecarboxamideand(3R,4R)—N-(2,3-difluorophenyl)-3-(hydroxymethyl)-1-methyl-2-oxo-4-[4-(trifluoromethyl)phenyl]-3-pyrrolidinecarboxamide(i.e. the products of Synthesis Example 1) (0.080 g, 0.19 mmol) andpyridine (0.020 mL, 0.22 mmol) were dissolved in dichloromethane (1.0mL). Acetyl chloride (0.015 mL, 0.22 mmol) was added and the solutionwas stirred at 23° C. for 20 min. The reaction mixture was concentratedonto silica gel and purified by column chromatography, eluting with 0%to 50% ethyl acetate in hexanes, to afford the title compound, acompound of the present invention, as a pale yellow oil (0.045 g).

¹H NMR δ 10.51 (br s, 1H), 7.55-7.44 (m, 3H), 7.31-7.26 (m, 2H),6.94-6.81 (m, 2H), 4.81 (d, J=10.9 Hz, 1H), 4.47 (d, J=10.9 Hz, 1H),4.06-3.98 (m, 1H), 3.65-3.59 (m, 1H), 3.35-3.29 (m, 1H), 3.05 (s, 3H),2.10 (s, 3H).

Synthesis Example 3 Preparation of(3S,4R)-3-acetyl-N-(2,3-difluorophenyl)-1-methyl-2-oxo-4-[4-(trifluoromethyl)phenyl]-3-pyrrolidinecarboxamide(Compound 3) Step A: Preparation of(3S,4R)-3-acetyl-N-(2,3-difluorophenyl)-1-methyl-2-oxo-4-[4-(trifluoromethyl)phenyl]-3-pyrrolidinecarboxamide

(3S,4S)—N-(2,3-difluorophenyl)-1-methyl-2-oxo-4-methyl-2-oxo-4-[4-(trifluoromethyl)phenyl]-3-pyrrolidinecarboxamide(0.10 g, 0.25 mmol) was dissolved in tetrahydrofuran (10 mL) and cooledto 0° C. A solution of lithium bis(trimethylsilyl)amide intetrahydrofuran (1.0 M, 0.50 mL, 0.50 mmol) was added and stirred at 0°C. for 10 min. Acetyl chloride (0.020 mL, 0.28 mmol) was added. Thereaction was warmed to 23° C. and stirred for 20 min. The reactionmixture was concentrated onto silica gel and purified by columnchromatography, eluting with 0% to 50% ethyl acetate in hexanes, toafford the title compound, a compound of the present invention, as acolorless solid (0.021 g).

¹H NMR δ 10.62 (br s, 1H), 7.51 (d, J=8.0 Hz, 2H), 7.40-7.33 (m, 1H),7.28 (d, J=8.2 Hz, 2H), 6.95-6.84 (m, 2H), 4.38-4.34 (m, 1H), 4.04-3.98(m, 1H), 3.06 (s, 3H), 2.42 (s, 3H).

By the procedures described herein together with methods known in theart, the following compounds of Tables 1 to 1008 can be prepared. Thefollowing abbreviations are used in the Tables which follow: i meansiso, c means cyclo, Me means methyl, Et means ethyl, Pr means propyl, Bumeans butyl, c-Pr cyclopropyl, c-Bu means cyclobutyl, Ph means phenyl,OMe means methoxy, OEt means ethoxy, Py means pyridinyl, —NO₂ meansnitro.

TABLE 1

L is L-1; R^(A) is Me; Q² is Ph(2-F); and Q¹ is; Q¹ Q¹ Q¹ Ph(3-Cl)Ph(3-CF₃) Ph(3-OCF₂H) Ph(3-F) Ph(3-CHF₂) Ph(3-OMe) Ph(3-Br) Ph(3-CH₂F)Ph(3-OCF₂CF₂H) Ph(3-Me) Ph(3-OCF₃) Ph(4-Cl) Ph(4-F) 2-Py(6-F)4-Py(2-Me,6-F) Ph(4-Br) 2-Py(6-CF₃) 4-Py(2-OMe,6-F) Ph(4-Me) 2-Py(6-Me)4-Py(2-OEt,6-F) Ph(4-CF₃) 2-Py(5-F) 4-Py(2,6-di-F) Ph(4-CHF₂)2-Py(5-CF₃) 4-Py(2-Me,6-CH₂F) Ph(4-CH₂F) 2-Py(5-Me) 4-Py(2-OMe,6-CH₂F)Ph(4-OCF₃) 2-Py(4-F) 4-Py(2-OEt,6-CH₂F) Ph(4-OCF₂H) 2-Py(4-CF₃)4-Py(2-F,6-CH₂F) Ph(4-OMe) 2-Py(4-Me) 4-Py(2-Me,6-OCHF₂) Ph(4-OCF₂CF₂H)2-Py(3-F) 4-Py(2-OMe,6-OCHF₂) Ph(2,3-di-F) 2-Py(3-CF₃)4-Py(2-OEt,6-OCHF₂) Ph(2,4-di-F) 2-Py(3-Me) 4-Py(2-F,6-OCHF₂)Ph(2,5-di-F) 3-Py 2-Thienyl Ph(2,6-di-F) 3-Py(6-F) 2-Thienyl(4-CF₃)Ph(3,4-di-F) 3-Py(6-CF₃) 2-Thienyl(5-CF₃) Ph(3,5-di-F) 3-Py(6-Me)3-Thienyl Ph(3-Me,4-F) 3-Py(5-F) 3-Thienyl(4-CF₃) Ph(3-F,4-Me)3-Py(5-CF₃) 3-Thienyl(5-CF₃) Ph(3-CF₃,4-F) 3-Py(5-Me) 2-FurylPh(3-F,4-CF₃) 3-Py(4-F) 2-Furyl(4-CF₃) Ph(3-CHF₂,4-F) 3-Py(4-CF₃)2-Furyl(5-CF₃) Ph(3-CH₂F,4-F) 3-Py(4-Me) 3-Furyl Ph(3,5-di-Et) 3-Py(2-F)3-Furyl(4-CF₃) Ph(3-Me,5-OMe) 3-Py(2-CF₃) 3-Furyl(5-CF₃) Ph(3,5-di-OMe)3-Py(2-Me) Pyrazin-2-yl Ph(3-OMe,5-OEt) 4-Py Pyrazin-2-yl(5-CF₃)Ph(3-Me,5-CH₂F) 4-Py(3-F) Pyrimidin-2-yl Ph(3-OMe,5-CH₂F) 4-Py(3-CF₃)Pyrimidin-2-yl(5-CF₃) Ph(3-OEt,5-CH₂F) 4-Py(3-Me) Pyrimidin-5-ylPh(2,3,4-tri-F) 4-Py(2-F) Pyrimidin-5-yl(2-CF₃) Ph(3,4,5-tri-F)4-Py(2-CF₃) 1,3-Dioxolan-4-yl 2-Py 4-Py(2-OMe,6-OEt)2,2-di-F-1,3-Dioxolan-4-yl

Table 2 is constructed in the same manner as Table 1 except that the RowHeading “L is L-1; R^(A) is Me; Q² is Ph(2-F); and Q¹ is” is replacedwith the Row Heading listed for Table 2 below (i.e. “L is L-1; R^(A) isMe; Q² is Ph(2,3-di-F); and Q¹ is”). Therefore the first entry in Table2 is a compound of Formula 1 wherein J is —CH₂—; Q² is Ph(2,3-di-F); Q¹is Ph(3-Cl) (i.e. 3-chlorophenyl); Y¹ is O; Y² is O; R⁷ is H; R⁹ is H; Lis L-1; and R^(A) is Me. Tables 3 through 16 are constructed similarly.

Table Row Heading 2 L is L-1; R^(A) is Me; Q² is Ph(2,3-di-F); and Q¹ is3 L is L-1; R^(A) is Me; Q² is Ph(2,4-di-F); and Q¹ is 4 L is L-1; R^(A)is Me; Q² is Ph(2,3,4-tri-F); and Q¹ is 5 L is L-1; R^(A) is Me; Q² isPh(2-CF₃); and Q¹ is 6 L is L-1; R^(A) is Me; Q² is Ph(2-Me); and Q¹ is7 L is L-1; R^(A) is Me; Q² is Ph(2-NO₂); and Q¹ is 8 L is L-1; R^(A) isMe; Q² is Ph(2-Cl); and Q¹ is 9 L is L-1; R^(A) is Me; Q² isPh(2-SO₂Me); and Q¹ is 10 L is L-1; R^(A) is Me; Q² is Ph(2-F,3-Cl); andQ¹ is 11 L is L-1; R^(A) is Me; Q² is Ph(2-SOMe); and Q¹ is 12 L is L-1;R^(A) is Me; Q² is Ph(2-SMe); and Q¹ is 13 L is L-1; R^(A) is Me; Q² isPh(2-Me,3-F); and Q¹ is 14 L is L-1; R^(A) is Me; Q² is3-Pyridinyl(2,6-di-F); and Q¹ is 15 L is L-1; R^(A) is Me; Q² is3-Pyridinyl(2-F); and Q¹is 16 L is L-1; R^(A) is Me; Q² is2-Pyridinyl(6-F); and Q¹ is

Table 17 through 1008

Tables 17 through 1008 are constructed the same way as Tables 1 through16 except that the part of the Row Heading referring to the identity ofL, “L is L-1; R^(A) is Me”, is replaced with the part of the Row Headingreferring to the identity of L listed for Tables 17 through 32 below(i.e. “L is L-1; R^(A) is Et”). Therefore the first entry in Table 17 isa compound of Formula 1 wherein J is —CH₂—; Q² is Ph(2,3-di-F); Q¹ isPh(3-Cl) (i.e. 3-chlorophenyl); Y¹ is O; Y² is O; R⁷ is H; R⁹ is H; L isL-1; and R^(A) is Et.

Tables Row Heading 17-32 L is L-1; R^(A) is Me 33-48 L is L-1; R^(A) isEt 49-64 L is L-1; R^(A) is n-Pr 65-80 L is L-1; R^(A) is i-Pr 81-96 Lis L-1; R^(A) is c-Pr  97-112 L is L-1; R^(A) is n-Bu 113-128 L is L-1;R^(A)is CF₃ 129-144 L is L-1; R^(A) is CCl₃ 145-160 L is L-1; R^(A) isPh 161-176 L is L-1; R^(A) is Ph(2-Me) 177-192 L is L-1; R^(A) isPh(3-Me) 193-208 L is L-1; R^(A) is Ph(4-Me) 209-224 L is L-1; R^(A) isOMe 225-240 L is L-1; R^(A) is OEt 241-256 L is L-2; R^(B) is H; R^(C)is H; R^(D) is H; R^(E) is Me 257-272 L is L-2; R^(B) is H; R^(C) is H;R^(D) is H; R^(E) is Et 273-288 L is L-2; R^(B) is H; R^(C) is H; R^(D)is H; R^(E) is n-Pr 289-304 L is L-2; R^(B) is H; R^(C) is H; R^(D) isH; R^(E) is c-Pr 305-320 L is L-2; R^(B) is H; R^(C) is H; R^(D) is H;R^(E) is COMe 321-336 L is L-2; R^(B) is H; R^(C) is H; R^(D) is H;R^(E) is COPh 337-352 L is L-2; R^(B) is H; R^(C) is H; R^(D) is H;R^(E) is COOMe 353-368 L is L-2; R^(B) is H; R^(C) is H; R^(D) is H;R^(E) is COOEt 369-384 L is L-2; R^(B) is H; R^(C) is H; R^(D) is H;R^(E) is SO₂Me 385-400 L is L-2; R^(B) is H; R^(C) is H; R^(D) is H;R^(E) is SO₂Ph 401-416 L is L-2; R^(B) is H; R^(C) is H; R^(D) is Me;R^(E) is Me 417-432 L is L-2; R^(B) is H; R^(C) is H; R^(D) is Me; R^(E)is Et 433-448 L is L-2; R^(B) is H; R^(C) is H; R^(D) is Me; R^(E) isn-Pr 449-464 L is L-2; R^(B) is H; R^(C) is H; R^(D) is Me; R^(E) isc-Pr 465-480 L is L-2; R^(B) is H; R^(C) is H; R^(D) is Me; R^(E) isCOMe 481-496 L is L-2; R^(B) is H; R^(C) is H; R^(D) is Me; R^(E) isCOPh 497-512 L is L-2; R^(B) is H; R^(C) is H; R^(D) is Me; R^(E) isCOOMe 513-528 L is L-2; R^(B) is H; R^(C) is H; R^(D) is Me; R^(E) isCOOEt 529-544 L is L-2; R^(B) is H; R^(C) is H; R^(D) is Me; R^(E) isSO₂Me 545-560 L is L-2; R^(B) is H; R^(C) is H; R^(D) is Me; R^(E) isSO₂Ph 561-576 L is L-2; R^(B) is H; R^(C) is H; R^(D) is Et; R^(E) is Me577-592 L is L-2; R^(B) is H; R^(C) is H; R^(D) is Et; R^(E) is Et593-608 L is L-2; R^(B) is H; R^(C) is H; R^(D) is Et; R^(E) is n-Pr609-624 L is L-2; R^(B) is H; R^(C) is H; R^(D) is Et; R^(E) is c-Pr625-640 L is L-2; R^(B) is H; R^(C) is H; R^(D) is Et; R^(E) is COMe641-656 L is L-2; R^(B) is H; R^(C) is H; R^(D) is Et; R^(E) is COPh657-672 L is L-2; R^(B) is H; R^(C) is H; R^(D) is Et; R^(E) is COOMe673-688 L is L-2; R^(B) is H; R^(C) is H; R^(D) is Et; R^(E) is COOEt689-704 L is L-2; R^(B) is H; R^(C) is H; R^(D) is Et; R^(E) is SO₂Me705-720 L is L-2; R^(B) is H; R^(C) is H; R^(D) is Et; R^(E) is SO₂Ph721-736 L is L-3; R^(B) is H; R^(C) is H; R^(F) is COMe 737-752 L isL-3; R^(B) is H; R^(C) is H; R^(F) is COCF₃ 753-768 L is L-3; R^(B) isH; R^(C) is H; R^(F) is COPh 769-784 L is L-3; R^(B) is H; R^(C) is H;R^(F) is COOMe 785-800 L is L-3; R^(B) is H; R^(C) is H; R^(F) is COOEt801-816 L is L-3; R^(B) is H; R^(C) is H; R^(F) is SO₂Me 817-832 L isL-3; R^(B) is H; R^(C) is H; R^(F) is SO₂Ph 833-848 L is L-3; R^(B) isH; R^(C) is H; R^(F) is PO(OH)₂ 849-864 L is L-3; R^(B) is H; R^(C) isH; R^(F) is PO(OMe)₂ 865-880 L is L-4; Both R^(B)'s are each H; BothR^(C)'s are each H; R^(G) is COMe 881-896 L is L-4; Both R^(B)'s areeach H; Both R^(C)'s are each H; R^(G) is COCF₃ 897-912 L is L-4; BothR^(B)'s are each H; Both R^(C)'s are each H; R^(G) is COPh 913-928 L isL-4; Both R^(B)'s are each H; Both R^(C)'s are each H; R^(G) is COOMe929-944 L is L-4; Both R^(B)'s are each H; Both R^(C)'s are each H;R^(G) is COOEt 945-960 L is L-4; Both R^(B)'s are each H; Both R^(C)'sare each H; R^(G) is SO₂Me 961-976 L is L-4; Both R^(B)'s are each H;Both R^(C)'s are each H; R^(G) is SO₂Ph 977-992 L is L-4; Both R^(B)'sare each H; Both R^(C)'s are each H; R^(G) is PO(OH)₂  993-1008 L isL-4; Both R^(B)'s are each H; Both R^(C)'s are each H; R^(G) is PO(OMe)₂

A compound of this invention will generally be used as a herbicidalactive ingredient in a composition, i.e. formulation, with at least oneadditional component selected from the group consisting of surfactants,solid diluents and liquid diluents, which serves as a carrier. Theformulation or composition ingredients are selected to be consistentwith the physical properties of the active ingredient, mode ofapplication and environmental factors such as soil type, moisture andtemperature.

Useful formulations include both liquid and solid compositions. Liquidcompositions include solutions (including emulsifiable concentrates),suspensions, emulsions (including microemulsions, oil-in-wateremulsions, flowable concentrates and/or suspoemulsions) and the like,which optionally can be thickened into gels. The general types ofaqueous liquid compositions are soluble concentrate, suspensionconcentrate, capsule suspension, concentrated emulsion, microemulsion,oil-in-water emulsion, flowable concentrate and suspo-emulsion. Thegeneral types of nonaqueous liquid compositions are emulsifiableconcentrate, microemulsifiable concentrate, dispersible concentrate andoil dispersion.

The general types of solid compositions are dusts, powders, granules,pellets, prills, pastilles, tablets, filled films (including seedcoatings) and the like, which can be water-dispersible (“wettable”) orwater-soluble. Films and coatings formed from film-forming solutions orflowable suspensions are particularly useful for seed treatment. Activeingredient can be (micro)encapsulated and further formed into asuspension or solid formulation; alternatively the entire formulation ofactive ingredient can be encapsulated (or “overcoated”). Encapsulationcan control or delay release of the active ingredient. An emulsifiablegranule combines the advantages of both an emulsifiable concentrateformulation and a dry granular formulation. High-strength compositionsare primarily used as intermediates for further formulation.

Sprayable formulations are typically extended in a suitable mediumbefore spraying. Such liquid and solid formulations are formulated to bereadily diluted in the spray medium, usually water, but occasionallyanother suitable medium like an aromatic or paraffinic hydrocarbon orvegetable oil. Spray volumes can range from about from about one toseveral thousand liters per hectare, but more typically are in the rangefrom about ten to several hundred liters per hectare. Sprayableformulations can be tank mixed with water or another suitable medium forfoliar treatment by aerial or ground application, or for application tothe growing medium of the plant. Liquid and dry formulations can bemetered directly into drip irrigation systems or metered into the furrowduring planting.

The formulations will typically contain effective amounts of activeingredient, diluent and surfactant within the following approximateranges which add up to 100 percent by weight.

Weight Percent Active Ingredient Diluent Surfactant Water-Dispersibleand Water- 0.001-90 0-99.999 0-15 soluble Granules, Tablets and PowdersOil Dispersions, Suspensions,    1-50 40-99    0-50 Emulsions, Solutions(including Emulsifiable Concentrates) Dusts    1-25 70-99    0-5 Granules and Pellets 0.001-99 5-99.999 0-15 High Strength Compositions  90-99 0-10    0-2 

Solid diluents include, for example, clays such as bentonite,montmorillonite, attapulgite and kaolin, gypsum, cellulose, titaniumdioxide, zinc oxide, starch, dextrin, sugars (e.g., lactose, sucrose),silica, talc, mica, diatomaceous earth, urea, calcium carbonate, sodiumcarbonate and bicarbonate, and sodium sulfate. Typical solid diluentsare described in Watkins et al., Handbook of Insecticide Dust Diluentsand Carriers, 2nd Ed., Dorland Books, Caldwell, N.J.

Liquid diluents include, for example, water, N,N-dimethylalkanamides(e.g., N,N-dimethylformamide), limonene, dimethyl sulfoxide,N-alkylpyrrolidones (e.g., N-methylpyrrolidinone), alkyl phosphates(e.g., triethyl phosphate), ethylene glycol, triethylene glycol,propylene glycol, dipropylene glycol, polypropylene glycol, propylenecarbonate, butylene carbonate, paraffins (e.g., white mineral oils,normal paraffins, isoparaffins), alkylbenzenes, alkylnaphthalenes,glycerine, glycerol triacetate, sorbitol, aromatic hydrocarbons,dearomatized aliphatics, alkylbenzenes, alkylnaphthalenes, ketones suchas cyclohexanone, 2-heptanone, isophorone and4-hydroxy-4-methyl-2-pentanone, acetates such as isoamyl acetate, hexylacetate, heptyl acetate, octyl acetate, nonyl acetate, tridecyl acetateand isobornyl acetate, other esters such as alkylated lactate esters,dibasic esters, alkyl and aryl benzoates and γ-butyrolactone, andalcohols, which can be linear, branched, saturated or unsaturated, suchas methanol, ethanol, n-propanol, isopropyl alcohol, n-butanol, isobutylalcohol, n-hexanol, 2-ethylhexanol, n-octanol, decanol, isodecylalcohol, isooctadecanol, cetyl alcohol, lauryl alcohol, tridecylalcohol, oleyl alcohol, cyclohexanol, tetrahydrofurfuryl alcohol,diacetone alcohol, cresol and benzyl alcohol. Liquid diluents alsoinclude glycerol esters of saturated and unsaturated fatty acids(typically C₆-C₂₂), such as plant seed and fruit oils (e.g., oils ofolive, castor, linseed, sesame, corn (maize), peanut, sunflower,grapeseed, safflower, cottonseed, soybean, rapeseed, coconut and palmkernel), animal-sourced fats (e.g., beef tallow, pork tallow, lard, codliver oil, fish oil), and mixtures thereof. Liquid diluents also includealkylated fatty acids (e.g., methylated, ethylated, butylated) whereinthe fatty acids may be obtained by hydrolysis of glycerol esters fromplant and animal sources, and can be purified by distillation. Typicalliquid diluents are described in Marsden, Solvents Guide, 2nd Ed.,Interscience, New York, 1950.

The solid and liquid compositions of the present invention often includeone or more surfactants. When added to a liquid, surfactants (also knownas “surface-active agents”) generally modify, most often reduce, thesurface tension of the liquid. Depending on the nature of thehydrophilic and lipophilic groups in a surfactant molecule, surfactantscan be useful as wetting agents, dispersants, emulsifiers or defoamingagents.

Surfactants can be classified as nonionic, anionic or cationic. Nonionicsurfactants useful for the present compositions include, but are notlimited to: alcohol alkoxylates such as alcohol alkoxylates based onnatural and synthetic alcohols (which may be branched or linear) andprepared from the alcohols and ethylene oxide, propylene oxide, butyleneoxide or mixtures thereof; amine ethoxylates, alkanolamides andethoxylated alkanolamides; alkoxylated triglycerides such as ethoxylatedsoybean, castor and rapeseed oils; alkylphenol alkoxylates such asoctylphenol ethoxylates, nonylphenol ethoxylates, dinonyl phenolethoxylates and dodecyl phenol ethoxylates (prepared from the phenolsand ethylene oxide, propylene oxide, butylene oxide or mixturesthereof); block polymers prepared from ethylene oxide or propylene oxideand reverse block polymers where the terminal blocks are prepared frompropylene oxide; ethoxylated fatty acids; ethoxylated fatty esters andoils; ethoxylated methyl esters; ethoxylated tristyrylphenol (includingthose prepared from ethylene oxide, propylene oxide, butylene oxide ormixtures thereof); fatty acid esters, glycerol esters, lanolin-basedderivatives, polyethoxylate esters such as polyethoxylated sorbitanfatty acid esters, polyethoxylated sorbitol fatty acid esters andpolyethoxylated glycerol fatty acid esters; other sorbitan derivativessuch as sorbitan esters; polymeric surfactants such as randomcopolymers, block copolymers, alkyd peg (polyethylene glycol) resins,graft or comb polymers and star polymers; polyethylene glycols (pegs);polyethylene glycol fatty acid esters; silicone-based surfactants; andsugar-derivatives such as sucrose esters, alkyl polyglycosides and alkylpolysaccharides.

Useful anionic surfactants include, but are not limited to: alkylarylsulfonic acids and their salts; carboxylated alcohol or alkylphenolethoxylates; diphenyl sulfonate derivatives; lignin and ligninderivatives such as lignosulfonates; maleic or succinic acids or theiranhydrides; olefin sulfonates; phosphate esters such as phosphate estersof alcohol alkoxylates, phosphate esters of alkylphenol alkoxylates andphosphate esters of styryl phenol ethoxylates; protein-basedsurfactants; sarcosine derivatives; styryl phenol ether sulfate;sulfates and sulfonates of oils and fatty acids; sulfates and sulfonatesof ethoxylated alkylphenols; sulfates of alcohols; sulfates ofethoxylated alcohols; sulfonates of amines and amides such asN,N-alkyltaurates; sulfonates of benzene, cumene, toluene, xylene, anddodecyl and tridecylbenzenes; sulfonates of condensed naphthalenes;sulfonates of naphthalene and alkyl naphthalene; sulfonates offractionated petroleum; sulfosuccinamates; and sulfosuccinates and theirderivatives such as dialkyl sulfosuccinate salts.

Useful cationic surfactants include, but are not limited to: amides andethoxylated amides; amines such as N-alkyl propanediamines,tripropylenetriamines and dipropylenetetramines, and ethoxylated amines,ethoxylated diamines and propoxylated amines (prepared from the aminesand ethylene oxide, propylene oxide, butylene oxide or mixturesthereof); amine salts such as amine acetates and diamine salts;quaternary ammonium salts such as quaternary salts, ethoxylatedquaternary salts and diquaternary salts; and amine oxides such asalkyldimethylamine oxides and bis-(2-hydroxyethyl)-alkylamine oxides.

Also useful for the present compositions are mixtures of nonionic andanionic surfactants or mixtures of nonionic and cationic surfactants.Nonionic, anionic and cationic surfactants and their recommended usesare disclosed in a variety of published references includingMcCutcheon's Emulsifiers and Detergents, annual American andInternational Editions published by McCutcheon's Division, TheManufacturing Confectioner Publishing Co.; Sisely and Wood, Encyclopediaof Surface Active Agents, Chemical Publ. Co., Inc., New York, 1964; andA. S. Davidson and B. Milwidsky, Synthetic Detergents, Seventh Edition,John Wiley and Sons, New York, 1987.

Compositions of this invention may also contain formulation auxiliariesand additives, known to those skilled in the art as formulation aids(some of which may be considered to also function as solid diluents,liquid diluents or surfactants). Such formulation auxiliaries andadditives may control: pH (buffers), foaming during processing(antifoams such polyorganosiloxanes), sedimentation of activeingredients (suspending agents), viscosity (thixotropic thickeners),in-container microbial growth (antimicrobials), product freezing(antifreezes), color (dyes/pigment dispersions), wash-off (film formersor stickers), evaporation (evaporation retardants), and otherformulation attributes. Film formers include, for example, polyvinylacetates, polyvinyl acetate copolymers, polyvinylpyrrolidone-vinylacetate copolymer, polyvinyl alcohols, polyvinyl alcohol copolymers andwaxes. Examples of formulation auxiliaries and additives include thoselisted in McCutcheon's Volume 2: Functional Materials, annualInternational and North American editions published by McCutcheon'sDivision, The Manufacturing Confectioner Publishing Co.; and PCTPublication WO 03/024222.

The compound of Formula 1 and any other active ingredients are typicallyincorporated into the present compositions by dissolving the activeingredient in a solvent or by grinding in a liquid or dry diluent.Solutions, including emulsifiable concentrates, can be prepared bysimply mixing the ingredients. If the solvent of a liquid compositionintended for use as an emulsifiable concentrate is water-immiscible, anemulsifier is typically added to emulsify the active-containing solventupon dilution with water. Active ingredient slurries, with particlediameters of up to 2,000 m can be wet milled using media mills to obtainparticles with average diameters below 3 m. Aqueous slurries can be madeinto finished suspension concentrates (see, for example, U.S. Pat. No.3,060,084) or further processed by spray drying to formwater-dispersible granules. Dry formulations usually require dry millingprocesses, which produce average particle diameters in the 2 to 10 mrange. Dusts and powders can be prepared by blending and usuallygrinding (such as with a hammer mill or fluid-energy mill). Granules andpellets can be prepared by spraying the active material upon preformedgranular carriers or by agglomeration techniques. See Browning,“Agglomeration”, Chemical Engineering, Dec. 4, 1967, pp 147-48, Perry'sChemical Engineer's Handbook, 4th Ed., McGraw-Hill, New York, 1963,pages 8-57 and following, and WO 91/13546. Pellets can be prepared asdescribed in U.S. Pat. No. 4,172,714. Water-dispersible andwater-soluble granules can be prepared as taught in U.S. Pat. Nos.4,144,050, 3,920,442 and DE 3,246,493. Tablets can be prepared as taughtin U.S. Pat. Nos. 5,180,587, 5,232,701 and 5,208,030. Films can beprepared as taught in GB 2,095,558 and U.S. Pat. No. 3,299,566.

For further information regarding the art of formulation, see T. S.Woods, “The Formulator's Toolbox—Product Forms for Modern Agriculture”in Pesticide Chemistry and Bioscience, The Food—Environment Challenge,T. Brooks and T. R. Roberts, Eds., Proceedings of the 9th InternationalCongress on Pesticide Chemistry, The Royal Society of Chemistry,Cambridge, 1999, pp. 120-133. See also U.S. Pat. No. 3,235,361, Col. 6,line 16 through Col. 7, line 19 and Examples 10-41; U.S. Pat. No.3,309,192, Col. 5, line 43 through Col. 7, line 62 and Examples 8, 12,15, 39, 41, 52, 53, 58, 132, 138-140, 162-164, 166, 167 and 169-182;U.S. Pat. No. 2,891,855, Col. 3, line 66 through Col. 5, line 17 andExamples 1-4; Klingman, Weed Control as a Science, John Wiley and Sons,Inc., New York, 1961, pp 81-96; Hance et al., Weed Control Handbook, 8thEd., Blackwell Scientific Publications, Oxford, 1989; and Developmentsin formulation technology, PJB Publications, Richmond, U K, 2000.

In the following Examples, all percentages are by weight and allformulations are prepared in conventional ways. Compound numbers referto compounds in Index Table A. Without further elaboration, it isbelieved that one skilled in the art using the preceding description canutilize the present invention to its fullest extent. The followingExamples are, therefore, to be construed as merely illustrative, and notlimiting of the disclosure in any way whatsoever. Percentages are byweight except where otherwise indicated.

Example A

High Strength Concentrate Compound 1 98.5% silica aerogel 0.5% syntheticamorphous fine silica 1.0%

Example B

Wettable Powder Compound 1 65.0% dodecylphenol polyethylene glycol ether2.0% sodium ligninsulfonate 4.0% sodium silicoaluminate 6.0%montmorillonite (calcined) 23.0%

Example C

Granule Compound 1 10.0% attapulgite granules (low volatile matter,0.71/0.30 mm; 90.0% U.S.S. No. 25-50 sieves)

Example D

Extruded Pellet Compound 1 25.0% anhydrous sodium sulfate 10.0% crudecalcium ligninsulfonate 5.0% sodium alkylnaphthalenesulfonate 1.0%calcium/magnesium bentonite 59.0%

Example E

Emulsifiable Concentrate Compound 1 10.0% polyoxyethylene sorbitolhexoleate 20.0% C₆-C₁₀ fatty acid methyl ester 70.0%

Example F

Microemulsion Compound 1 5.0% polyvinylpyrrolidone-vinyl acetatecopolymer 30.0% alkylpolyglycoside 30.0% glyceryl monooleate 15.0% water20.0%

Example G

Suspension Concentrate Compound 1  35% butylpolyoxyethylene/polypropylene block copolymer 4.0% stearicacid/polyethylene glycol copolymer 1.0% styrene acrylic polymer 1.0%xanthan gum 0.1% propylene glycol 5.0% silicone based defoamer 0.1%l,2-benzisothiazolin-3-one 0.1% water 53.7% 

Example H

Emulsion in Water Compound 1 10.0% butyl polyoxyethylene/polypropyleneblock copolymer 4.0% stearic acid/polyethylene glycol copolymer 1.0%styrene acrylic polymer 1.0% xanthan gum 0.1% propylene glycol 5.0%silicone based defoamer 0.1% l,2-benzisothiazolin-3-one 0.1% aromaticpetroleum based hydrocarbon 20.0 water 58.7%

Example I

Oil Dispersion Compound 1 25% polyoxyethylene sorbitol hexaoleate 15%organically modified bentonite clay 2.5%  fatty acid methyl ester 57.5% 

The present disclosure also includes Examples A through I above except“Compound 1” is replaced with “Compound 2” and “Compound 3”. “Compound4”, “Compound 5”, “Compound 6”, “Compound 7”, “Compound 8” or “Compound9” above. Test results indicate that the compounds of the presentinvention are highly active preemergent and/or postemergent herbicidesand/or plant growth regulants. The compounds of the invention generallyshow highest activity for postemergence weed control (i.e. applied afterweed seedlings emerge from the soil) and preemergence weed control (i.e.applied before weed seedlings emerge from the soil). Many of them haveutility for broad-spectrum pre- and/or postemergence weed control inareas where complete control of all vegetation is desired such as aroundfuel storage tanks, industrial storage areas, parking lots, drive-intheaters, air fields, river banks, irrigation and other waterways,around billboards and highway and railroad structures. Many of thecompounds of this invention, by virtue of selective metabolism in cropsversus weeds, or by selective activity at the locus of physiologicalinhibition in crops and weeds, or by selective placement on or withinthe environment of a mixture of crops and weeds, are useful for theselective control of grass and broadleaf weeds within a crop/weedmixture. One skilled in the art will recognize that the preferredcombination of these selectivity factors within a compound or group ofcompounds can readily be determined by performing routine biologicaland/or biochemical assays. Compounds of this invention may showtolerance to important agronomic crops including, but is not limited to,alfalfa, barley, cotton, wheat, rape, sugar beets, corn (maize),sorghum, soybeans, rice, oats, peanuts, vegetables, tomato, potato,perennial plantation crops including coffee, cocoa, oil palm, rubber,sugarcane, citrus, grapes, fruit trees, nut trees, banana, plantain,pineapple, hops, tea and forests such as eucalyptus and conifers (e.g.,loblolly pine), and turf species (e.g., Kentucky bluegrass, St.Augustine grass, Kentucky fescue and Bermuda grass). Compounds of thisinvention can be used in crops genetically transformed or bred toincorporate resistance to herbicides, express proteins toxic toinvertebrate pests (such as Bacillus thuringiensis toxin), and/orexpress other useful traits. Those skilled in the art will appreciatethat not all compounds are equally effective against all weeds.Alternatively, the subject compounds are useful to modify plant growth.

As the compounds of the invention have both preemergent and postemergentherbicidal activity, to control undesired vegetation by killing orinjuring the vegetation or reducing its growth, the compounds can beusefully applied by a variety of methods involving contacting aherbicidally effective amount of a compound of the invention, or acomposition comprising said compound and at least one of a surfactant, asolid diluent or a liquid diluent, to the foliage or other part of theundesired vegetation or to the environment of the undesired vegetationsuch as the soil or water in which the undesired vegetation is growingor which surrounds the seed or other propagule of the undesiredvegetation. Undesired vegetation includes at least one selected from thegroup consisting of grass weeds and broadleaf weeds. Undesiredvegetation is selected from the group consisting of annual bluegrass,Benghal dayflower, blackgrass, black nightshade, broadleaf signalgrass,Canada thistle, cheat, common cocklebur (Xanthium pensylvanicum), commonragweed, corn poppies, field violet, giant foxtail, goosegrass, greenfoxtail, guinea grass, hairy beggarticks, herbicide-resistant blackgrass, horseweed, Italian rye grass, jimsonweed, Johnson grass (Sorghumhalepense), large crabgrass, little seed canary grass, morning glory,Pennsylvania smartweed, pitted morning glory, prickly sida, quackgrass,redroot pigweed, shattercane, shepherd's purse, silky windgrass,sunflower (as a weed in a potato crop), wild buckwheat (Polygonumconvolvulus), wild mustard (Brassica kaber), wild oat (Avena fatua),wild pointsettia, yellow foxtail, and yellow nutsedge (Cyperusesculentus).

A herbicidally effective amount of the compounds of this invention isdetermined by a number of factors. These factors include: formulationselected, method of application, amount and type of vegetation present,growing conditions, etc. In general, a herbicidally effective amount ofcompounds of this invention is about 0.001 to 20 kg/ha with a preferredrange of about 0.004 to 1 kg/ha. One skilled in the art can easilydetermine the herbicidally effective amount necessary for the desiredlevel of weed control.

In one common embodiment, a compound of the invention is applied,typically in a formulated composition, to a locus comprising desiredvegetation (e.g., crops) and undesired vegetation (i.e. weeds), both ofwhich may be seeds, seedlings and/or larger plants, in contact with agrowth medium (e.g., soil). In this locus, a composition comprising acompound of the invention can be directly applied to a plant or a partthereof, particularly of the undesired vegetation, and/or to the growthmedium in contact with the plant.

Plant varieties and cultivars of the desired vegetation in the locustreated with a compound of the invention can be obtained by conventionalpropagation and breeding methods or by genetic engineering methods.Genetically modified plants (transgenic plants) are those in which aheterologous gene (transgene) has been stably integrated into theplant's genome. A transgene that is defined by its particular locationin the plant genome is called a transformation or transgenic event.

Genetically modified plant cultivars in the locus which can be treatedaccording to the invention include those that are resistant against oneor more biotic stresses (pests such as nematodes, insects, mites, fungi,etc.) or abiotic stresses (drought, cold temperature, soil salinity,etc.), or that contain other desirable characteristics. Plants can begenetically modified to exhibit traits of, for example, herbicidetolerance, insect-resistance, modified oil profiles or droughttolerance.

Although most typically, compounds of the invention are used to controlundesired vegetation, contact of desired vegetation in the treated locuswith compounds of the invention may result in super-additive orsynergistic (enhanced) effects with genetic traits in the desiredvegetation, including traits incorporated through genetic modification.For example, resistance to phytophagous insect pests or plant diseases,tolerance to biotic/abiotic stresses or storage stability may be greaterthan expected from the genetic traits in the desired vegetation.

Compounds of this invention can also be mixed with one or more otherbiologically active compounds or agents including herbicides, herbicidesafeners, fungicides, insecticides, nematocides, bactericides,acaricides, growth regulators such as insect molting inhibitors androoting stimulants, chemosterilants, semiochemicals, repellents,attractants, pheromones, feeding stimulants, plant nutrients, otherbiologically active compounds or entomopathogenic bacteria, virus orfungi to form a multi-component pesticide giving an even broaderspectrum of agricultural protection. Mixtures of the compounds of theinvention with other herbicides can broaden the spectrum of activityagainst additional weed species, and suppress the proliferation of anyresistant biotypes. Thus the present invention also pertains to acomposition comprising a compound of Formula 1 (in a herbicidallyeffective amount) and at least one additional biologically activecompound or agent (in a biologically effective amount) and can furthercomprise at least one of a surfactant, a solid diluent or a liquiddiluent. The other biologically active compounds or agents can beformulated in compositions comprising at least one of a surfactant,solid or liquid diluent. For mixtures of the present invention, one ormore other biologically active compounds or agents can be formulatedtogether with a compound of Formula 1, to form a premix, or one or moreother biologically active compounds or agents can be formulatedseparately from the compound of Formula 1, and the formulations combinedtogether before application (e.g., in a spray tank) or, alternatively,applied in succession.

A mixture of one or more of the following herbicides with a compound ofthis invention may be particularly useful for weed control: acetochlor,acifluorfen and its sodium salt, aclonifen, acrolein (2-propenal),alachlor, alloxydim, ametryn, amicarbazone, amidosulfuron,aminocyclopyrachlor and its esters (e.g., methyl, ethyl) and salts(e.g., sodium, potassium), aminopyralid, amitrole, ammonium sulfamate,anilofos, asulam, atrazine, azimsulfuron, beflubutamid, S-beflubutamide,benazolin, benazolin-ethyl, bencarbazone, benfluralin, benfuresate,bensulfuron-methyl, bensulide, bentazone, benzobicyclon, benzofenap,bicyclopyrone, bifenox, bilanafos, bispyribac and its sodium salt,bromacil, bromobutide, bromofenoxim, bromoxynil, bromoxynil octanoate,butachlor, butafenacil, butamifos, butralin, butroxydim, butylate,cafenstrole, carbetamide, carfentrazone-ethyl, catechin, chlomethoxyfen,chloramben, chlorbromuron, chlorflurenol-methyl, chloridazon,chlorimuron-ethyl, chlorotoluron, chlorpropham, chlorsulfuron,chlorthal-dimethyl, chlorthiamid, cinidon-ethyl, cinmethylin,cinosulfuron, clacyfos, clefoxydim, clethodim, clodinafop-propargyl,clomazone, clomeprop, clopyralid, clopyralid-olamine,cloransulam-methyl, cumyluron, cyanazine, cycloate, cyclopyranil,cyclopyrimorate, cyclosulfamuron, cycloxydim, cyhalofop-butyl, 2,4-D andits butotyl, butyl, isoctyl and isopropyl esters and itsdimethylammonium, diolamine and trolamine salts, daimuron, dalapon,dalapon-sodium, dazomet, 2,4-DB and its dimethylammonium, potassium andsodium salts, desmedipham, desmetryn, dicamba and its diglycolammonium,dimethylammonium, potassium and sodium salts, dichlobenil, dichlorprop,diclofop-methyl, diclosulam, difenzoquat metilsulfate, diflufenican,diflufenzopyr, dimefuron, dimepiperate, dimethachlor, dimethametryn,dimethenamid, dimethenamid-P, dimethipin, dimethylarsinic acid and itssodium salt, dinitramine, dinoterb, diphenamid, diquat dibromide,dithiopyr, diuron, DNOC, endothal, EPTC, esprocarb, ethalfluralin,ethametsulfuron-methyl, ethiozin, ethofumesate, ethoxyfen,ethoxysulfuron, etobenzanid, fenoxaprop-ethyl, fenoxaprop-P-ethyl,fenoxasulfone, fenquinotrione, fentrazamide, fenuron, fenuron-TCA,flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, flazasulfuron,florasulam, fluazifop-butyl, fluazifop-P-butyl, fluazolate,flucarbazone, flucetosulfuron, fluchloralin, flufenacet, flufenpyr,flufenpyr-ethyl, flumetsulam, flumiclorac-pentyl, flumioxazin,fluometuron, fluoroglycofen-ethyl, flupoxam, flupyrsulfuron-methyl andits sodium salt, flurenol, flurenol-butyl, fluridone, flurochloridone,fluroxypyr, flurtamone, fluthiacet-methyl, fomesafen, foramsulfuron,fosamine-ammonium, glufosinate, glufosinate-ammonium, glufosinate-P,glyphosate and its salts such as ammonium, isopropylammonium, potassium,sodium (including sesquisodium) and trimesium (alternatively namedsulfosate), halauxifen, halauxifen-methyl, halosulfuron-methyl,haloxyfop-etotyl, haloxyfop-methyl, hexazinone, hydantocidin,imazamethabenz-methyl, imazamox, imazapic, imazapyr, imazaquin,imazaquin-ammonium, imazethapyr, imazethapyr-ammonium, imazosulfuron,indanofan, indaziflam, iofensulfuron, iodosulfuron-methyl, ioxynil,ioxynil octanoate, ioxynil-sodium, ipfencarbazone, isoproturon, isouron,isoxaben, isoxaflutole, isoxachlortole, lactofen, lenacil, linuron,maleic hydrazide, MCPA and its salts (e.g., MCPA-dimethylammonium,MCPA-potassium and MCPA-sodium, esters (e.g., MCPA-2-ethylhexyl,MCPA-butotyl) and thioesters (e.g., MCPA-thioethyl), MCPB and its salts(e.g., MCPB-sodium) and esters (e.g., MCPB-ethyl), mecoprop, mecoprop-P,mefenacet, mefluidide, mesosulfuron-methyl, mesotrione, metam-sodium,metamifop, metamitron, metazachlor, metazosulfuron, methabenzthiazuron,methylarsonic acid and its calcium, monoammonium, monosodium anddisodium salts, methyldymron, metobenzuron, metobromuron, metolachlor,S-metolachlor, metosulam, metoxuron, metribuzin, metsulfuron-methyl,molinate, monolinuron, naproanilide, napropamide, napropamide-M,naptalam, neburon, nicosulfuron, norflurazon, orbencarb,orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxasulfuron,oxaziclomefone, oxyfluorfen, paraquat dichloride, pebulate, pelargonicacid, pendimethalin, penoxsulam, pentanochlor, pentoxazone, perfluidone,pethoxamid, pethoxyamid, phenmedipham, picloram, picloram-potassium,picolinafen, pinoxaden, piperophos, pretilachlor, primisulfuron-methyl,prodiamine, profoxydim, prometon, prometryn, propachlor, propanil,propaquizafop, propazine, propham, propisochlor, propoxycarbazone,propyrisulfuron, propyzamide, prosulfocarb, prosulfuron, pyraclonil,pyraflufen-ethyl, pyrasulfotole, pyrazogyl, pyrazolynate, pyrazoxyfen,pyrazosulfuron-ethyl, pyribenzoxim, pyributicarb, pyridate, pyriftalid,pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyrithiobac-sodium,pyroxasulfone, pyroxsulam, quinclorac, quinmerac, quinoclamine,quizalofop-ethyl, quizalofop-P-ethyl, quizalofop-P-tefuryl, rimsulfuron,saflufenacil, sethoxydim, siduron, simazine, simetryn, sulcotrione,sulfentrazone, sulfometuron-methyl, sulfosulfuron, 2,3,6-TBA, TCA,TCA-sodium, tebutam, tebuthiuron, tefuryltrione, tembotrione,tepraloxydim, terbacil, terbumeton, terbuthylazine, terbutryn,thenylchlor, thiazopyr, thiencarbazone, thifensulfuron-methyl,thiobencarb, tiafenacil, tiocarbazil, tolpyralate, topramezone,tralkoxydim, tri-allate, triafamone, triasulfuron, triaziflam,tribenuron-methyl, triclopyr, triclopyr-butotyl,triclopyr-triethylammonium, tridiphane, trietazine, trifloxysulfuron,trifludimoxazin, trifluralin, triflusulfuron-methyl, tritosulfuron,vernolate,3-(2-chloro-3,6-difluorophenyl)-4-hydroxy-1-methyl-1,5-naphthyridin-2(1H)-one,5-chloro-3-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-1-(4-methoxyphenyl)-2(1H)-quinoxalinone,2-chloro-N-(1-methyl-1H-tetrazol-5-yl)-6-(trifluoromethyl)-3-pyridinecarboxamide,7-(3,5-dichloro-4-pyridinyl)-5-(2,2-difluoroethyl)-8-hydroxypyrido[2,3-b]pyrazin-6(5H)-one),4-(2,6-diethyl-4-methylphenyl)-5-hydroxy-2,6-dimethyl-3(2H)-pyridazinone),5-[[(2,6-difluorophenyl)methoxy]methyl]-4,5-dihydro-5-methyl-3-(3-methyl-2-thienyl)isoxazole(previously methioxolin),4-(4-fluorophenyl)-6-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-2-methyl-1,2,4-triazine-3,5(2H,4H)-dione,methyl4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoro-2-pyridinecarboxylate,2-methyl-3-(methylsulfonyl)-N-(1-methyl-1H-tetrazol-5-yl)-4-(trifluoromethyl)benzamideand2-methyl-N-(4-methyl-1,2,5-oxadiazol-3-yl)-3-(methylsulfinyl)-4-(trifluoromethyl)benzamide.Other herbicides also include bioherbicides such as Alternaria destruensSimmons, Colletotrichum gloeosporiodes (Penz.) Penz. & Sacc., Drechsieramonoceras (MTB-951), Myrothecium verrucaria (Albertini & Schweinitz)Ditmar: Fries, Phytophthora palmivora (Butl.) Butl. and Pucciniathlaspeos Schub.

Preferred for better control of undesired vegetation (e.g., lower userate such as from greater-than-additive effects, broader spectrum ofweeds controlled, or enhanced crop safety) or for preventing thedevelopment of resistant weeds are mixtures of a compound of thisinvention with a herbicide selected from the group consisting ofatrazine, azimsulfuron, beflubutamid, S-beflubutamide F4050,benzisothiazolinone, carfentrazone-ethyl, chlorimuron-ethyl,chlorsulfuron-methyl, clomazone, clopyralid potassium,cloransulam-methyl,2-[(2,5-dichlorophenyl)methyl]-4,4-dimethyl-3-isoxazolidinone F9600,ethametsulfuron-methyl, flumetsulam,4-(4-fluorophenyl)-6-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-2-methyl-1,2,4-triazine-3,5-(2H,4H)-dioneF9960, flupyrsulfuron-methyl, fluthiacet-methyl, fomesafen, imazethapyr,lenacil, mesotrione, metribuzin, metsulfuron-methyl, pethoxamid,picloram, pyroxasulfone, quinclorac, rimsulfuron, S-metolachlor,sulfentrazone, thifensulfuron-methyl, triflusulfuron-methyl andtribenuron-methyl.

Compounds of this invention can also be used in combination with plantgrowth regulators such as aviglycine, N-(phenylmethyl)-1H-purin-6-amine,epocholeone, gibberellic acid, gibberellin A₄ and A₇, harpin protein,mepiquat chloride, prohexadione calcium, prohydrojasmon, sodiumnitrophenolate and trinexapac-methyl, and plant growth modifyingorganisms such as Bacillus cereus strain BP01.

General references for agricultural protectants (i.e. herbicides,herbicide safeners, insecticides, fungicides, nematocides, acaricidesand biological agents) include The Pesticide Manual, 13th Edition, C. D.S. Tomlin, Ed., British Crop Protection Council, Farnham, Surrey, U. K.,2003 and The BioPesticide Manual, 2nd Edition, L. G. Copping, Ed.,British Crop Protection Council, Farnham, Surrey, U. K., 2001.

For embodiments where one or more of these various mixing partners areused, the mixing partners are typically used in the amounts similar toamounts customary when the mixture partners are used alone. Moreparticularly in mixtures, active ingredients are often applied at anapplication rate between one-half and the full application ratespecified on product labels for use of active ingredient alone. Theseamounts are listed in references such as The Pesticide Manual and TheBioPesticide Manual. The weight ratio of these various mixing partners(in total) to the compound of Formula 1 is typically between about1:3000 and about 3000:1. Of note are weight ratios between about 1:300and about 300:1 (for example ratios between about 1:30 and about 30:1).One skilled in the art can easily determine through simpleexperimentation the biologically effective amounts of active ingredientsnecessary for the desired spectrum of biological activity. It will beevident that including these additional components may expand thespectrum of weeds controlled beyond the spectrum controlled by thecompound of Formula 1 alone.

In certain instances, combinations of a compound of this invention withother biologically active (particularly herbicidal) compounds or agents(i.e. active ingredients) can result in a greater-than-additive (i.e.synergistic (enhanced)) effect on weeds and/or a less-than-additiveeffect (i.e. safening) on crops or other desirable plants. Reducing thequantity of active ingredients released in the environment whileensuring effective pest control is always desirable. Ability to usegreater amounts of active ingredients to provide more effective weedcontrol without excessive crop injury is also desirable. When synergism(enhanced effects) of herbicidal active ingredients occurs on weeds atapplication rates giving agronomically satisfactory levels of weedcontrol, such combinations can be advantageous for reducing cropproduction cost and decreasing environmental load. When safening ofherbicidal active ingredients occurs on crops, such combinations can beadvantageous for increasing crop protection by reducing weedcompetition.

Of note is a combination of a compound of the invention with at leastone other herbicidal active ingredient. Of particular note is such acombination where the other herbicidal active ingredient has differentsite of action from the compound of the invention. In certain instances,a combination with at least one other herbicidal active ingredienthaving a similar spectrum of control but a different site of action willbe particularly advantageous for resistance management. Thus, acomposition of the present invention can further comprise (in aherbicidally effective amount) at least one additional herbicidal activeingredient having a similar spectrum of control but a different site ofaction.

Compounds of this invention can also be used in combination withherbicide safeners such as allidochlor, benoxacor, cloquintocet-mexyl,cumyluron, cyometrinil, cyprosulfonamide, daimuron, dichlormid,dicyclonon, dietholate, dimepiperate, fenchlorazole-ethyl, fenclorim,flurazole, fluxofenim, furilazole, isoxadifen-ethyl, mefenpyr-diethyl,mephenate, methoxyphenone, naphthalic anhydride (1,8-naphthalicanhydride), oxabetrinil, N-(aminocarbonyl)-2-methylbenzenesulfonamide,N-(aminocarbonyl)-2-fluorobenzenesulfonamide,1-bromo-4-[(chloromethyl)sulfonyl]benzene (BCS),4-(dichloroacetyl)-1-oxa-4-azospiro[4.5]decane (MON 4660),2-(dichloromethyl)-2-methyl-1,3-dioxolane (MG 191), ethyl1,6-dihydro-1-(2-methoxyphenyl)-6-oxo-2-phenyl-5-pyrimidinecarboxylate,2-hydroxy-N,N-dimethyl-6-(trifluoromethyl)pyridine-3-carboxamide, and3-oxo-1-cyclohexen-1-yl1-(3,4-dimethylphenyl)-1,6-dihydro-6-oxo-2-phenyl-5-pyrimidinecarboxylate,2,2-dichloro-1-(2,2,5-trimethyl-3-oxazolidinyl)-ethanone and2-methoxy-N-[[4-[[(methylamino)carbonyl]amino]phenyl]sulfonyl]-benzamideto increase safety to certain crops. Antidotally effective amounts ofthe herbicide safeners can be applied at the same time as the compoundsof this invention, or applied as seed treatments. Therefore an aspect ofthe present invention relates to a herbicidal mixture comprising acompound of this invention and an antidotally effective amount of aherbicide safener. Seed treatment is particularly useful for selectiveweed control, because it physically restricts antidoting to the cropplants. Therefore a particularly useful embodiment of the presentinvention is a method for selectively controlling the growth ofundesired vegetation in a crop comprising contacting the locus of thecrop with a herbicidally effective amount of a compound of thisinvention wherein seed from which the crop is grown is treated with anantidotally effective amount of safener. Antidotally effective amountsof safeners can be easily determined by one skilled in the art throughsimple experimentation.

Compounds of the invention cans also be mixed with: (1) polynucleotidesincluding but not limited to DNA, RNA, and/or chemically modifiednucleotides influencing the amount of a particular target through downregulation, interference, suppression or silencing of the geneticallyderived transcript that render a herbicidal effect; or (2)polynucleotides including but not limited to DNA, RNA, and/or chemicallymodified nucleotides influencing the amount of a particular targetthrough down regulation, interference, suppression or silencing of thegenetically derived transcript that render a safening effect.

Of note is a composition comprising a compound of the invention (in aherbicidally effective amount), at least one additional activeingredient selected from the group consisting of other herbicides andherbicide safeners (in an effective amount), and at least one componentselected from the group consisting of surfactants, solid diluents andliquid diluents.

Table A1 lists specific combinations of a Component (a) with Component(b) illustrative of the mixtures, compositions and methods of thepresent invention. Compound 1 (i.e. “Cmpd. No.” stands for “CompoundNumber”) in the Component (a) column is identified in Index Table A. Thesecond column of Table A1 lists the specific Component (b) compound(e.g., “2,4-D” in the first line). The third, fourth and fifth columnsof Table A1 lists ranges of weight ratios for rates at which theComponent (a) compound is typically applied to a field-grown croprelative to Component (b) (i.e. (a):(b)). Thus, for example, the firstline of Table A1 specifically discloses the combination of Component (a)(i.e. Compound 1 in Index Table A) with 2,4-D is typically applied in aweight ratio between 1:192-6:1. The remaining lines of Table A1 are tobe construed similarly.

TABLE A1 Component (a) Typical More Typical Most Typical (Cmpd. No.)Component (b) Weight Ratio Weight Ratio Weight Ratio 1 2,4-D 1:192-6:11:64-2:1 1:24-1:3 1 Acetochlor 1:768-2:1 1:256-1:2   1:96-1:11 1Acifluorfen  1:96-12:1 1:32-4:1 1:12-1:2 1 Aclonifen 1:857-2:11:285-1:3  1:107-1:12 1 Alachlor 1:768-2:1 1:256-1:2   1:96-1:11 1Ametryn 1:384-3:1 1:128-1:1  1:48-1:6 1 Amicarbazone 1:192-6:1 1:64-2:11:24-1:3 1 Amidosulfuron   1:6-168:1  1:2-56:1  1:1-11:1 1Aminocyclopyrachlor  1:48-24:1 1:16-8:1  1:6-2:1 1 Aminopyralid 1:20-56:1  1:6-19:1  1:2-4:1 1 Amitrole 1:768-2:1 1:256-1:2   1:96-1:111 Anilofos  1:96-12:1 1:32-4:1 1:12-1:2 1 Asulam 1:960-2:1 1:320-1:3 1:120-1:14 1 Atrazine 1:192-6:1 1:64-2:1 1:24-1:3 1 Azimsulfuron  1:6-168:1  1:2-56:1  1:1-11:1 1 Beflubutamid 1:342-4:1 1:114-2:1 1:42-1:5 1 S-Beflubutamid  1:171-4:0.5  1:57-2:0.5  1:21-1:2.5 1Benfuresate 1:617-2:1 1:205-1:2  1:77-1:9 1 Bensulfuron-methyl 1:25-45:1  1:8-15:1  1:3-3:1 1 Bentazone 1:192-6:1 1:64-2:1 1:24-1:3 1Benzobicyclon  1:85-14:1 1:28-5:1 1:10-1:2 1 Benzofenap 1:257-5:11:85-2:1 1:32-1:4 1 Bicyclopyrone  1:42-27:1 1:14-9:1  1:5-2:1 1 Bifenox1:257-5:1 1:85-2:1 1:32-1:4 1 Bispyribac-sodium   1:10-112:1  1:3-38:1 1:1-7:1 1 Bromacil 1:384-3:1 1:128-1:1  1:48-1:6 1 Bromobutide1:384-3:1 1:128-1:1  1:48-1:6 1 Bromoxynil  1:96-12:1 1:32-4:1 1:12-1:21 Butachlor 1:768-2:1 1:256-1:2   1:96-1:11 1 Butafenacil  1:42-27:11:14-9:1  1:5-2:1 1 Butylate 1:1542-1:2  1:514-1:5  1:192-1:22 1Carfenstrole 1:192-6:1 1:64-2:1 1:24-1:3 1 Carfentrazone-ethyl 1:128-9:11:42-3:1 1:16-1:2 1 Chlorimuron-ethyl   1:8-135:1  1:2-45:1  1:1-9:1 1Chlorotoluron 1:768-2:1 1:256-1:2   1:96-1:11 1 Chlorsulfuron  1:6-168:1  1:2-56:1  1:1-11:1 1 Cincosulfuron  1:17-68:1  1:5-23:1 1:2-5:1 1 Cinidon-ethyl 1:384-3:1 1:128-1:1  1:48-1:6 1 Cinmethylin 1:34-34:1  1:11-12:1  1:4-3:1 1 Clacyfos  1:34-34:1  1:11-12:1  1:4-3:11 Clethodim  1:48-24:1 1:16-8:1  1:6-2:1 1 Clodinafop-propargyl 1:20-56:1  1:6-19:1  1:2-4:1 1 Clomazone 1:384-3:1 1:128-1:1  1:48-1:61 Clomeprop 1:171-7:1 1:57-3:1 1:21-1:3 1 Clopyralid 1:192-6:1 1:64-2:11:24-1:3 1 Cloransulam-methyl  1:12-96:1  1:4-32:1  1:1-6:1 1 Cumyluron1:384-3:1 1:128-1:1  1:48-1:6 1 Cyanazine 1:384-3:1 1:128-1:1  1:48-1:61 Cyclopyrimorate  1:17-68:1  1:5-23:1  1:2-5:1 1 Cyclosulfamuron 1:17-68:1  1:5-23:1  1:2-5:1 1 Cycloxydim  1:96-12:1 1:32-4:1 1:12-1:21 Cyhalofop  1:25-45:1  1:8-15:1  1:3-3:1 1 Daimuron 1:192-6:1 1:64-2:11:24-1:3 1 Desmedipham 1:322-4:1 1:107-2:1  1:40-1:5 1 Dicamba 1:192-6:11:64-2:1 1:24-1:3 1 Dichlobenil 1:1371-1:2  1:457-1:4  1:171-1:20 1Dichlorprop 1:925-2:1 1:308-1:3  1:115-1:13 1 Diclofop-methyl 1:384-3:11:128-1:1  1:48-1:6 1 Diclosulam   1:10-112:1  1:3-38:1  1:1-7:1 1Difenzoquat 1:288-4:1 1:96-2:1 1:36-1:4 1 Diflufenican 1:857-2:11:285-1:3  1:107-1:12 1 Diflufenzopyr  1:12-96:1  1:4-32:1  1:1-6:1 1Dimethachlor 1:768-2:1 1:256-1:2   1:96-1:11 1 Dimethametryn 1:192-6:11:64-2:1 1:24-1:3 1 Dimethenamid-P 1:384-3:1 1:128-1:1  1:48-1:6 1Dithiopyr 1:192-6:1 1:64-2:1 1:24-1:3 1 Diuron 1:384-3:1 1:128-1:1 1:48-1:6 1 EPTC 1:768-2:1 1:256-1:2   1:96-1:11 1 Esprocarb 1:1371-1:2 1:457-1:4  1:171-1:20 1 Ethalfluralin 1:384-3:1 1:128-1:1  1:48-1:6 1Ethametsulfuron-methyl  1:17-68:1  1:5-23:1  1:2-5:1 1 Ethoxyfen  1:8-135:1  1:2-45:1  1:1-9:1 1 Ethoxysulfuron  1:20-56:1  1:6-19:1 1:2-4:1 1 Etobenzanid 1:257-5:1 1:85-2:1 1:32-1:4 1 Fenoxaprop-ethyl 1:120-10:1 1:40-4:1 1:15-1:2 1 Fenoxasulfone  1:85-14:1 1:28-5:11:10-1:2 1 Fenquinotrione  1:17-68:1  1:5-23:1  1:2-5:1 1 Fentrazamide 1:17-68:1  1:5-23:1  1:2-5:1 1 Flazasulfuron  1:17-68:1  1:5-23:1 1:2-5:1 1 Florasulam   1:2-420:1   1:1-140:1  2:1-27:1 1Fluazifop-butyl 1:192-6:1 1:64-2:1 1:24-1:3 1 Flucarbazone   1:8-135:1 1:2-45:1  1:1-9:1 1 Flucetosulfuron   1:8-135:1  1:2-45:1  1:1-9:1 1Flufenacet 1:257-5:1 1:85-2:1 1:32-1:4 1 Flumetsulam  1:24-48:1 1:8-16:1  1:3-3:1 1 Flumiclorac-pentyl   1:10-112:1  1:3-38:1  1:1-7:11 Flumioxazin  1:25-45:1  1:8-15:1  1:3-3:1 1 Fluometuron 1:384-3:11:128-1:1  1:48-1:6 1 Flupyrsulfuron-methyl   1:3-336:1   1:1-112:1 2:1-21:1 1 Fluridone 1:384-3:1 1:128-1:1  1:48-1:6 1 Fluroxypyr 1:96-12:1 1:32-4:1 1:12-1:2 1 Flurtamone 1:857-2:1 1:285-1:3 1:107-1:12 1 Fluthiacet-methyl  1:48-42:1  1:16-14:1  1:3-3:1 1Fomesafen  1:96-12:1 1:32-4:1 1:12-1:2 1 Foramsulfuron  1:13-84:1 1:4-28:1  1:1-6:1 1 Glufosinate 1:288-4:1 1:96-2:1 1:36-1:4 1Glyphosate 1:288-4:1 1:96-2:1 1:36-1:4 1 Halosulfuron-methyl  1:17-68:1 1:5-23:1  1:2-5:1 1 Halauxifen  1:20-56:1  1:6-19:1  1:2-4:1 1Halauxifen methyl  1:20-56:1  1:6-19:1  1:2-4:1 1 Haloxyfop-methyl 1:34-34:1  1:11-12:1  1:4-3:1 1 Hexazinone 1:192-6:1 1:64-2:1 1:24-1:31 Hydantocidin 1:1100-16:1 1:385-8:1  1:144-4:1  1 Imazamox  1:13-84:1 1:4-28:1  1:1-6:1 1 Imazapic  1:20-56:1  1:6-19:1  1:2-4:1 1 Imazapyr 1:85-14:1 1:28-5:1 1:10-1:2 1 Imazaquin  1:34-34:1  1:11-12:1  1:4-3:11 Imazethabenz-methyl 1:171-7:1 1:57-3:1 1:21-1:3 1 Imazethapyr 1:24-48:1  1:8-16:1  1:3-3:1 1 Imazosulfuron  1:27-42:1  1:9-14:1 1:3-3:1 1 Indanofan 1:342-4:1 1:114-2:1  1:42-1:5 1 Indaziflam 1:25-45:1  1:8-15:1  1:3-3:1 1 Iodosulfuron-methyl   1:3-336:1  1:1-112:1  2:1-21:1 1 Ioxynil 1:192-6:1 1:64-2:1 1:24-1:3 1Ipfencarbazone  1:85-14:1 1:28-5:1 1:10-1:2 1 Isoproturon 1:384-3:11:128-1:1  1:48-1:6 1 Isoxaben 1:288-4:1 1:96-2:1 1:36-1:4 1Isoxaflutole  1:60-20:1 1:20-7:1  1:7-2:1 1 Lactofen  1:42-27:1 1:14-9:1 1:5-2:1 1 Lenacil 1:384-3:1 1:128-1:1  1:48-1:6 1 Linuron 1:384-3:11:128-1:1  1:48-1:6 1 MCPA 1:192-6:1 1:64-2:1 1:24-1:3 1 MCPB 1:288-4:11:96-2:1 1:36-1:4 1 Mecoprop 1:768-2:1 1:256-1:2   1:96-1:11 1 Mefenacet1:384-3:1 1:128-1:1  1:48-1:6 1 Mefluidide 1:192-6:1 1:64-2:1 1:24-1:3 1Mesosulfuron-methyl   1:5-224:1  1:1-75:1  1:1-14:1 1 Mesotrione 1:42-27:1 1:14-9:1  1:5-2:1 1 Metamifop  1:42-27:1 1:14-9:1  1:5-2:1 1Metazachlor 1:384-3:1 1:128-1:1  1:48-1:6 1 Metazosulfuron  1:25-45:1 1:8-15:1  1:3-3:1 1 Methabenzthiazuron 1:768-2:1 1:256-1:2   1:96-1:111 Metolachlor 1:768-2:1 1:256-1:2   1:96-1:11 1 Metosulam   1:8-135:1 1:2-45:1  1:1-9:1 1 Metribuzin 1:192-6:1 1:64-2:1 1:24-1:3 1Metsulfuron-methyl   1:2-560:1   1:1-187:1  3:1-35:1 1 Molinate1:1028-2:1  1:342-1:3  1:128-1:15 1 Napropamide 1:384-3:1 1:128-1:1 1:48-1:6 1 Napropamide-M 1:192-6:1 1:64-2:1 1:24-1:3 1 Naptalam1:192-6:1 1:64-2:1 1:24-1:3 1 Nicosulfuron  1:12-96:1  1:4-32:1  1:1-6:11 Norflurazon 1:1152-1:1  1:384-1:3  1:144-1:16 1 Orbencarb 1:1371-1:2 1:457-1:4  1:171-1:20 1 Orthosulfamuron  1:20-56:1  1:6-19:1  1:2-4:1 1Oryzalin 1:514-3:1 1:171-1:2  1:64-1:8 1 Oxadiargyl 1:384-3:1 1:128-1:1 1:48-1:6 1 Oxadiazon 1:548-3:1 1:182-1:2  1:68-1:8 1 Oxasulfuron 1:27-42:1  1:9-14:1  1:3-3:1 1 Oxaziclomefone  1:42-27:1 1:14-9:1 1:5-2:1 1 Oxyfluorfen 1:384-3:1 1:128-1:1  1:48-1:6 1 Paraquat1:192-6:1 1:64-2:1 1:24-1:3 1 Pendimethalin 1:384-3:1 1:128-1:1 1:48-1:6 1 Penoxsulam   1:10-112:1  1:3-38:1  1:1-7:1 1 Penthoxamid1:384-3:1 1:128-1:1  1:48-1:6 1 Pentoxazone  1:102-12:1 1:34-4:11:12-1:2 1 Phenmedipham  1:102-12:1 1:34-4:1 1:12-1:2 1 Picloram 1:96-12:1 1:32-4:1 1:12-1:2 1 Picolinafen  1:34-34:1  1:11-12:1 1:4-3:1 1 Pinoxaden  1:25-45:1  1:8-15:1  1:3-3:1 1 Pretilachlor1:192-6:1 1:64-2:1 1:24-1:3 1 Primisulfuron-methyl   1:8-135:1  1:2-45:1 1:1-9:1 1 Prodiamine 1:384-3:1 1:128-1:1  1:48-1:6 1 Profoxydim 1:42-27:1 1:14-9:1  1:5-2:1 1 Prometryn 1:384-3:1 1:128-1:1  1:48-1:6 1Propachlor 1:1152-1:1  1:384-1:3  1:144-1:16 1 Propanil 1:384-3:11:128-1:1  1:48-1:6 1 Propaquizafop  1:48-24:1 1:16-8:1  1:6-2:1 1Propoxycarbazone  1:17-68:1  1:5-23:1  1:2-5:1 1 Propyrisulfuron 1:17-68:1  1:5-23:1  1:2-5:1 1 Propyzamide 1:384-3:1 1:128-1:1 1:48-1:6 1 Prosulfocarb 1:1200-1:2  1:400-1:4  1:150-1:17 1 Prosulfuron  1:6-168:1  1:2-56:1  1:1-11:1 1 Pyraclonil  1:42-27:1 1:14-9:1 1:5-2:1 1 Pyraflufen-ethyl   1:5-224:1  1:1-75:1  1:1-14:1 1Pyrasulfotole  1:13-84:1  1:4-28:1  1:1-6:1 1 Pyrazolynate 1:857-2:11:285-1:3  1:107-1:12 1 Pyrazosulfuron-ethyl   1:10-112:1  1:3-38:1 1:1-7:1 1 Pyrazoxyfen   1:5-224:1  1:1-75:1  1:1-14:1 1 Pyribenzoxim  1:10-112:1  1:3-38:1  1:1-7:1 1 Pyributicarb 1:384-3:1 1:128-1:1 1:48-1:6 1 Pyridate 1:288-4:1 1:96-2:1 1:36-1:4 1 Pyriftalid  1:10-112:1  1:3-38:1  1:1-7:1 1 Pyriminobac-methyl  1:20-56:1 1:6-19:1  1:2-4:1 1 Pyrimisulfan  1:17-68:1  1:5-23:1  1:2-5:1 1Pyrithiobac  1:24-48:1  1:8-16:1  1:3-3:1 1 Pyroxasulfone  1:85-14:11:28-5:1 1:10-1:2 1 Pyroxsulam   1:5-224:1  1:1-75:1  1:1-14:1 1Quinclorac 1:192-6:1 1:64-2:1 1:24-1:3 1 Quizalofop-ethyl  1:42-27:11:14-9:1  1:5-2:1 1 Rimsulfuron  1:13-84:1  1:4-28:1  1:1-6:1 1Saflufenacil  1:25-45:1  1:8-15:1  1:3-3:1 1 Sethoxydim  1:96-12:11:32-4:1 1:12-1:2 1 Simazine 1:384-3:1 1:128-1:1  1:48-1:6 1 Sulcotrione 1:120-10:1 1:40-4:1 1:15-1:2 1 Sulfentrazone 1:147-8:1 1:49-3:11:18-1:3 1 Sulfometuron-methyl  1:34-34:1  1:11-12:1  1:4-3:1 1Sulfosulfuron   1:8-135:1  1:2-45:1  1:1-9:1 1 Tebuthiuron 1:384-3:11:128-1:1  1:48-1:6 1 Tefuryltrione  1:42-27:1 1:14-9:1  1:5-2:1 1Tembotrione  1:31-37:1  1:10-13:1  1:3-3:1 1 Tepraloxydim  1:25-45:1 1:8-15:1  1:3-3:1 1 Terbacil 1:288-4:1 1:96-2:1 1:36-1:4 1Terbuthylazine 1:857-2:1 1:285-1:3  1:107-1:12 1 Terbutryn 1:192-6:11:64-2:1 1:24-1:3 1 Thenylchlor  1:85-14:1 1:28-5:1 1:10-1:2 1 Thiazopyr1:384-3:1 1:128-1:1  1:48-1:6 1 Thiencarbazone   1:3-336:1   1:1-112:1 2:1-21:1 1 Thifensulfuron-methyl   1:5-224:1  1:1-75:1  1:1-14:1 1Tiafenacil  1:17-68:1  1:5-23:1  1:2-5:1 1 Thiobencarb 1:768-2:11:256-1:2   1:96-1:11 1 Tolpyralate  1:31-37:1  1:10-13:1  1:3-3:1 1Topramzone   1:6-168:1  1:2-56:1  1:1-11:1 1 Tralkoxydim  1:68-17:11:22-6:1  1:8-2:1 1 Triafamone   1:2-420:1   1:1-140:1  2:1-27:1 1Triallate 1:768-2:1 1:256-1:2   1:96-1:11 1 Triasulfuron   1:5-224:1 1:1-75:1  1:1-14:1 1 Triaziflam 1:171-7:1 1:57-3:1 1:21-1:3 1Tribenuron-methyl   1:3-336:1   1:1-112:1  2:1-21:1 1 Triclopyr1:192-6:1 1:64-2:1 1:24-1:3 1 Trifloxysulfuron   1:2-420:1   1:1-140:1 2:1-27:1 1 Trifludimoxazin  1:25-45:1  1:8-15:1  1:3-3:1 1 Trifluralin1:288-4:1 1:96-2:1 1:36-1:4 1 Triflusulfuron-methyl  1:17-68:1  1:5-23:1 1:2-5:1 1 Tritosulfuron  1:13-84:1  1:4-28:1  1:1-6:1

Table A2 is constructed the same as Table A1 above except that entriesbelow the “Component (a)” column heading are replaced with therespective Component (a) Column Entry shown below. Compound 2 in theComponent (a) column is identified in Index Table A. Thus, for example,in Table A2 the entries below the “Component (a)” column heading allrecite “Compound 2” (i.e. Compound 2 identified in Index Table A), andthe first line below the column headings in Table A2 specificallydiscloses a mixture of Compound 2 with 2,4-D. Tables A3 through A11 areconstructed similarly.

Table Component (a) Number Column Entries A2 Compound 2 A3 Compound 3 A4Compound 4 A5 Compound 5 A6 Compound 6 A7 Compound 7 A8 Compound 8 A9Compound 9

Preferred for better control of undesired vegetation (e.g., lower userate such as from synergism (enhanced effects), broader spectrum ofweeds controlled, or enhanced crop safety) or for preventing thedevelopment of resistant weeds are mixtures of a compound of Formula 1with a herbicide selected from the group consisting ofchlorimuron-ethyl, nicosulfuron, mesotrione, thifensulfuron-methyl,flupyrsulfuron-methyl, tribenuron, pyroxasulfone, pinoxaden,tembotrione, pyroxsulam, metolachlor and S-metolachlor.

The following Tests demonstrate the control efficacy of the compounds ofthis invention against specific weeds. The weed control afforded by thecompounds is not limited, however, to these species. See Index Tables Afor compound descriptions. The following abbreviations are used in theIndex Table which follow: The abbreviation “Cmpd. No.” stands for“Compound Number”. The abbreviation “Ex.” stands for “Example” and isfollowed by a number indicating in which example the compound isprepared. Mass spectral data are reported with an estimated precisionwithin ±0.5 Da as the molecular weight of the highest isotopic abundanceparent ion (M+1) formed by addition of H⁺ (molecular weight of 1) to themolecule observed by using atmospheric pressure chemical ionization(AP+).

INDEX TABLE A

Cmpd. No. Q¹ Q² L R⁹ L 1 (Ex. 3) Ph(4-CF₃) Ph(2,3-di-F) L-1 H R^(A) =CH₃ 2 (Ex. 2) Ph(4-CF₃) Ph(2,3-di-F) L-3 H R^(B), R^(C) = H; R^(F) =C(═O)CH₃ 3 Ph(4-CF₃) Ph(2,3-di-F) L-1 —C(═O)C(CH₃)₂C(═O)— 4 (Ex. 1)(cis) Ph(4-CF₃) Ph(2,3-di-F) L-3 H R^(B); R^(C) = H; R^(F) = H 5 (Ex. 1)(trans) Ph(4-CF₃) Ph(2,3-di-F) L-3 H R^(B); R^(C) = H; R^(F) = H 6(trans) Ph(4-CF₃) Ph(2,3-di-F) L-3 H R^(B), R^(C) = H; R^(F) =C(═O)(CH₂)₃C(═O)OH 7 Ph(4-CF₃) Ph(2,3-di-F) L-1 H R^(A) = N(H)CH₂CH₃ 8Ph(4-CF₃) Ph(2,3-di-F) L-1 H R^(A) = N(H)CH(CH₃)₂ 9 Ph(4-CF₃)Ph(2,3-di-F) L-2 H R^(B); R^(C) = H; R^(D) = CH₃; R^(E) is CH₃

INDEX TABLE B Cmpd. No. Mass (M+) 1 * 2 * 3 495 (M + 1) 4 429 (M + 1) 5429 (M + 1) 6 529 (M + 1) 7 470 (M + 1) 8 484 (M + 1) 9 454 (M − 1) *See Synthesis Example for ¹H NMR data

Biological Examples of the Invention Test A

Seeds of plant species selected from barnyardgrass (Echinochloacrus-galli), kochia (Kochia scoparia), ragweed (common ragweed, Ambrosiaelatior), ryegrass, Italian (Italian ryegrass, Lolium multiflorum),foxtail, green (green foxtail, Setaria viridis), and pigweed (Amaranthusretroflexus) were planted into a blend of loam soil and sand and treatedpreemergence with a directed soil spray using test chemicals formulatedin a non-phytotoxic solvent mixture which included a surfactant.

At the same time, plants selected from these weed species and also wheat(Triticum aestivum), corn (Zea mays), blackgrass (Alopecurusmyosuroides), and galium (catchweed bedstraw, Galium aparine) wereplanted in pots containing the same blend of loam soil and sand andtreated with postemergence applications of test chemicals formulated inthe same manner. Plants ranged in height from 2 to 10 cm and were in theone- to two-leaf stage for the postemergence treatment. Treated plantsand untreated controls were maintained in a greenhouse for approximately10 d, after which time all treated plants were compared to untreatedcontrols and visually evaluated for injury. Plant response ratings,summarized in Table A, are based on a 0 to 100 scale where 0 is noeffect and 100 is complete control. A dash (-) response means no testresult.

TABLE A Postemergence Compounds 1 2 3 4 5 6 7 8 9 125 g ai/haBarnyardgrass 90 50 70 60 80 50 10 0 90 Blackgrass 50 10 30 40 30 0 0 060 Corn 80 40 80 50 60 0 0 0 50 Foxtail, Green 90 70 60 60 80 20 20 0 90Galium 60 40 50 40 40 0 30 0 60 Kochia 70 40 60 60 70 0 0 0 70 Pigweed80 40 60 70 50 0 30 0 80 Ragweed 40 40 40 0 40 0 0 0 30 Ryegrass,Italian 80 50 50 50 50 40 10 0 60 Wheat 50 20 40 20 30 10 0 0 60 31 gai/ha Barnyardgrass 70 0 40 0 30 0 0 0 70 Blackgrass  0 0 20 0 0 0 0 050 Corn 20 0 10 0 0 0 0 0 40 Foxtail, Green 50 20 0 10 30 0 0 0 50Galium 50 0 40 20 40 0 0 0 60 Kochia 20 0 0 0 30 0 0 0 50 Pigweed 30 2040 30 30 0 10 0 30 Ragweed  0 0 0 0 0 0 0 0 30 Ryegrass, Italian 60 2040 0 20 0 0 0 50 Wheat 20 0 0 0 0 0 0 0 30 Preemergence Compounds 1 2 34 5 6 7 8 9 125 g ai/ha Barnyardgrass 90 80 90 90 90 50 70 0 90 Foxtail,Green 90 90 90 90 90 80 80 0 90 Kochia 80 50 50 40 60 0 0 0 70 Pigweed90 80 100 90 60 0 10 0 80 Ragweed 70 30 20 0 60 0 0 0 60 Ryegrass,Italian 60 10 40 50 80 30 0 0 80 31 g ai/ha Barnyardgrass 80 50 80 30 8010 0 0 90 Foxtail, Green 90 60 90 50 70 30 0 0 90 Kochia 40 20 0 0 0 0 00 30 Pigweed 50 20 20 0 0 0 0 0 70 Ragweed 20 0 0 0 0 0 0 0  0 Ryegrass,Italian 30 0 20 0 10 0 0 0 60

Test B

Plant species in the flooded paddy test selected from rice (Oryzasativa), sedge, umbrella (small-flower umbrella sedge, Cyperusdifformis), ducksalad (Heteranthera limosa), and barnyardgrass(Echinochloa crus-galli) were grown to the 2-leaf stage for testing. Attime of treatment, test pots were flooded to 3 cm above the soilsurface, treated by application of test compounds directly to the paddywater, and then maintained at that water depth for the duration of thetest. Treated plants and controls were maintained in a greenhouse for 13to 15 d, after which time all species were compared to controls andvisually evaluated. Plant response ratings, summarized in Table B, arebased on a scale of 0 to 100 where 0 is no effect and 100 is completecontrol. A dash (-) response means no test result.

TABLE B Compounds 250 g ai/ha 1 2 3 4 5 6 7 8 9 Flood Barnyardgrass 7065 45 50 65 60 0 0 65 Ducksalad 90 95 80 95 90 85 75 0 95 Rice 0 30 10 025 20 30 0 0 Sedge, Umbrella 0 0 0 0 0 0 0 0 0

What is claimed is:
 1. A compound selected from Formula 1, N-oxides, andsalts thereof

wherein L is selected from

R^(A) is C₁-C₇ alkyl, C₁-C₇ haloalkyl, C₃-C₉ cycloalkyl, C₃-C₉halocycloalkyl, C₁-C₇ alkoxy, C₁-C₇ haloalkoxy, C₃-C₉ cycloalkoxy, C₃-C₉halocycloalkoxy, C₂-C₈ alkenyl, C₂-C₈ haloalkenyl, C₁-C₇ alkylamino,C₁-C₇ haloalkylamino, C₂-C₉ dialkylamino, C₂-C₉ halodialkylamino, C₃-C₉cycloalkylamino or C₃-C₉ halocycloalkylamino, each substituted orunsubstituted with up to 3 substituents independently selected from R⁸or G¹; or R^(A) is G¹ or OG¹; or R^(A) is taken together with R⁹ as—C(R^(I))(R^(J))C(═O)—; R^(B) is H, C₁-C₄ alkoxy, C₁-C₄ haloalkyl orC₁-C₄ alkyl; or phenyl substituted or unsubstituted with halogen orC₁-C₄ alkyl; R^(C) is H, C₁-C₄ alkoxy, C₁-C₄ haloalkyl or C₁-C₄ alkyl;or phenyl substituted or unsubstituted with halogen or C₁-C₄ alkyl;R^(D) is H, C₁-C₄ alkyl or C₂-C₄ alkylcarbonyl; R^(E) is H, hydroxy,amino, cyano, formyl, —C(O)NH₂, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₂-C₆cyanoalkyl, C₃-C₆ cycloalkyl, C₄-C₈ cycloalkylalkyl, C₂-C₈ alkoxyalkyl,C₃-C₈ alkoxyalkoxyalkyl, C₂-C₈ haloalkoxyalkyl, C₂-C₈ alkenyl, C₂-C₈haloalkenyl, C₂-C₈ alkenylalkyl, C₂-C₈ haloalkenylalkyl, C₂-C₈alkylcarbonyl, C₂-C₈ haloalkylcarbonyl, C₄-C₁₀ cycloalkylcarbonyl,C₅-C₁₀ cycloalkylcarbonylalkyl, C₂-C₈ alkoxycarbonyl, C₂-C₈haloalkoxycarbonyl, C₄-C₁₀ cycloalkoxycarbonyl, C₂-C₈alkylaminocarbonyl, C₃-C₁₀ dialkylaminocarbonyl, C₄-C₁₀cycloalkylaminocarbonyl, C₁-C₆ alkoxy, C₁-C₆ alkylsulfinyl, C₁-C₆haloalkylsulfinyl, C₃-C₈ cycloalkylsulfinyl, C₁-C₆ alkylsulfonyl, C₁-C₆haloalkylsulfonyl, C₃-C₈ cycloalkylsulfonyl, C₁-C₆ alkylaminosulfonyl orC₂-C₈ dialkylaminosulfonyl; or G^(E) or W^(E)G^(E); R^(F) is H, formyl,—C(O)NH₂, C₂-C₈ alkylcarbonyl, C₂-C₈ haloalkylcarbonyl, C₄-C₁₀cycloalkylcarbonyl, C₂-C₈ alkoxycarbonyl, C₂-C₈ haloalkoxycarbonyl,C₄-C₁₀ cycloalkoxycarbonyl, C₂-C₈ alkylaminocarbonyl, C₃-C₁₀dialkylaminocarbonyl, C₄-C₁₀ cycloalkylaminocarbonyl, C₁-C₆alkylsulfinyl, C₁-C₆ haloalkylsulfinyl, C₃-C₈ cycloalkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₆ haloalkylsulfonyl, C₃-C₈ cycloalkylsulfonyl, C₁-C₆alkylaminosulfonyl, C₂-C₈ dialkylaminosulfonyl, —P(═O)(OH)₂, C₁-C₆dialkylphosphoryl, C₁-C₆ haloalkylphosphoryl, C₃-C₈cycloalkylphosphoryl, C₂-C₈ dialkoxyphosphoryl, C₆-C₁₄dicycloalkoxyphosphoryl, C₈-C₁₆ dicycloalkylalkoxyphosphoryl, C₂-C₁₂bis(alkylamino)phosphoryl, C₄-C₂₄ bis(dialkylamino)phosphoryl; or G^(F)or W^(F)G^(F); R^(G) is formyl, —C(O)NH₂, C₂-C₈ alkylcarbonyl, C₂-C₈haloalkylcarbonyl, C₄-C₁₀ cycloalkylcarbonyl, C₂-C₈ alkoxycarbonyl,C₂-C₈ haloalkoxycarbonyl, C₄-C₁₀ cycloalkoxycarbonyl, C₂-C₈alkylaminocarbonyl, C₃-C₁₀ dialkylaminocarbonyl, C₄-C₁₀cycloalkylaminocarbonyl, C₁-C₆ alkylsulfinyl, C₁-C₆ haloalkylsulfinyl,C₃-C₈ cycloalkylsulfinyl, C₁-C₆ alkylsulfonyl, C₁-C₆ haloalkylsulfonyl,C₃-C₈ cycloalkylsulfonyl, C₁-C₆ alkylaminosulfonyl, C₂-C₈dialkylaminosulfonyl, —P(═O)(OH)₂, C₁-C₆ dialkylphosphoryl, C₁-C₆haloalkylphosphoryl, C₃-C₈ cycloalkylphosphoryl, C₂-C₈dialkoxyphosphoryl, C₆-C₁₄ dicycloalkoxyphosphoryl, C₈-C₁₆dicycloalkylalkoxyphosphoryl, C₂-C₁₂ bis(alkylamino)phosphoryl, C₄-C₂₄bis(dialkylamino)phosphoryl; or phenyl substituted or unsubstituted withR¹⁶; or W^(G)G^(G); R^(I) is H, C₁-C₄ alkoxy, C₁-C₄ haloalkyl or C₁-C₄alkyl; or phenyl substituted or unsubstituted with halogen or C₁-C₄alkyl; R^(J) is H, C₁-C₄ alkoxy, C₁-C₄ haloalkyl or C₁-C₄ alkyl; orphenyl substituted or unsubstituted with halogen or C₁-C₄ alkyl; Q¹ is aphenyl ring or a naphthalenyl ring system, each ring or ring systemsubstituted or unsubstituted with up to 5 substituents independentlyselected from R⁷; or a 4- to 7-membered heterocyclic ring; or an 8- to10-membered bicyclic ring system, each ring or ring system containingring members selected from carbon atoms and 1 to 5 heteroatomsindependently selected from up to 2 O, up to 2 S and up to 5 N atoms,wherein up to 3 carbon ring members are independently selected fromC(═O) and C(═S), and the sulfur atom ring members are independentlyselected from S(═O)_(u)(═NR¹⁴)_(v), each ring or ring system substitutedor unsubstituted with up to 5 substituents independently selected fromR¹⁰ on carbon atom ring members and selected from R¹² on nitrogen atomring members; or Q² is a phenyl ring or a naphthalenyl ring system, eachring or ring system substituted or unsubstituted with up to 5substituents independently selected from R¹⁰; or a 4- to 7-memberedheterocyclic ring; or an 8- to 10-membered bicyclic ring system, eachring or ring system containing ring members selected from carbon atomsand 1 to 4 heteroatoms independently selected from up to 2 O, up to 2 Sand up to 5 N atoms, wherein up to 3 carbon ring members areindependently selected from C(═O) and C(═S), and the sulfur atom ringmembers are independently selected from S(═O)_(u)(═NR¹⁴)_(v), each ringor ring system substituted or unsubstituted with up to 5 substituentsindependently selected from R¹¹ on carbon atom ring members and selectedfrom R¹³ on nitrogen atom ring members; or J is —CR²R³—, —CR²R³—CR⁴R⁵—,—NR⁶— or —O—; Y¹ and Y² are each independently O, S or NR¹⁵; R¹ is H,hydroxy, amino, cyano, formyl, C₃-C₈ alkylcarbonylalkyl, —C(C₁-C₄alkyl)=N—O(C₁-C₄ alkyl), —C(O)NH₂, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₂-C₆alkenyl, C₃-C₆ alkynyl, C₂-C₆ cyanoalkyl, C₃-C₆ cycloalkyl, C₃-C₈cycloalkenyl, C₄-C₈ cycloalkylalkyl, C₂-C₈ alkoxyalkyl, C₃-C₈alkoxyalkoxyalkyl, C₂-C₈ haloalkoxyalkyl, C₂-C₈ haloalkenylalkyl, C₂-C₈alkylthioalkyl, C₂-C₈ alkylsulfinylalkyl, C₂-C₈ alkylsulfonylalkyl,C₂-C₈ alkylcarbonyl, C₂-C₈ haloalkylcarbonyl, C₄-C₁₀ cycloalkylcarbonyl,C₅-C₁₀ cycloalkylcarbonylalkyl, C₂-C₈ alkoxycarbonyl, C₂-C₈haloalkoxycarbonyl, C₄-C₁₀ cycloalkoxycarbonyl, C₂-C₈alkylaminocarbonyl, C₃-C₁₀ dialkylaminocarbonyl, C₄-C₁₀cycloalkylaminocarbonyl, C₁-C₆ alkoxy, C₁-C₆ alkylthio, C₁-C₆haloalkylthio, C₃-C₈ cycloalkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆haloalkylsulfinyl, C₃-C₈ cycloalkylsulfinyl, C₁-C₆ alkylsulfonyl, C₁-C₆haloalkylsulfonyl, C₃-C₈ cycloalkylsulfonyl, C₁-C₆ alkylaminosulfonyl,C₂-C₈ dialkylaminosulfonyl, C₃-C₁₀ trialkylsilyl; or —CPh=N—O(C₁-C₄alkyl), each substituted or unsubstituted on ring members with up to 5substituents independently selected from R¹³; or G¹; R² and R³ are eachindependently H, halogen, hydroxy, C₁-C₄ alkyl, C₁-C₄ haloalkyl or C₁-C₄alkoxy; or R² and R³ are taken together with the carbon atom to whichthey are bonded to form a C₃-C₇ cycloalkyl ring; R⁴ and R⁵ are eachindependently H, halogen, hydroxy, C₁-C₄ alkyl, C₁-C₄ haloalkyl or C₁-C₄alkoxy; R⁶ is C₁-C₆ alkyl, C₂-C₆ alkenyl, C₃-C₆ alkynyl or C₁-C₆ alkoxy;or R¹ and R⁶ are taken together as C₃-C₆ alkylene or —CH₂OCH₂—; R⁷ is H,halogen, hydroxy, C₁-C₄ alkoxy, C₁-C₄ haloalkyl or C₁-C₄ alkyl; each R⁸is independently cyano, hydroxy, amino, nitro, —CHO, —C(═O)OH,—C(═O)NH₂, —SO₂NH₂, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₂-C₈ alkylcarbonyl,C₂-C₈ haloalkylcarbonyl, C₂-C₈ alkoxycarbonyl, C₄-C₁₀cycloalkoxycarbonyl, C₅-C₁₂ cycloalkylalkoxycarbonyl, C₂-C₈alkylaminocarbonyl, C₃-C₁₀ dialkylaminocarbonyl, C₁-C₆ alkoxy, C₁-C₆haloalkoxy, C₂-C₈ alkylcarbonyloxy, C₁-C₆ alkylthio, C₁-C₆haloalkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆ haloalkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₆ haloalkylsulfonyl, C₁-C₆ alkylaminosulfonyl, C₂-C₈dialkylaminosulfonyl, C₃-C₁₀ trialkylsilyl, C₁-C₆ alkylamino, C₂-C₈dialkylamino, C₂-C₈ alkylcarbonylamino or C₁-C₆ alkylsulfonylamino; R⁹is H, hydroxy, amino, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₂-C₆ alkenyl, C₃-C₆alkynyl, C₂-C₈ alkoxyalkyl, C₂-C₈ haloalkoxyalkyl, C₂-C₈ alkylthioalkyl,C₂-C₈ alkylsulfinylalkyl, C₂-C₈ alkylsulfonylalkyl, C₂-C₈ alkylcarbonyl,C₂-C₈ haloalkylcarbonyl, C₄-C₁₀ cycloalkylcarbonyl, C₂-C₈alkoxycarbonyl, C₂-C₈ haloalkoxycarbonyl, C₄-C₁₀ cycloalkoxycarbonyl,C₂-C₈ alkylaminocarbonyl, C₃-C₁₀ dialkylaminocarbonyl, C₄-C₁₀cycloalkylaminocarbonyl, C₁-C₆ alkoxy, C₁-C₆ alkylthio, C₁-C₆haloalkylthio, C₃-C₈ cycloalkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆haloalkylsulfinyl, C₃-C₈ cycloalkylsulfinyl, C₁-C₆ alkylsulfonyl, C₁-C₆haloalkylsulfonyl, C₃-C₈ cycloalkylsulfonyl, C₁-C₆ alkylaminosulfonyl,C₂-C₈ dialkylaminosulfonyl or C₃-C₁₀ trialkylsilyl or G¹; each R¹⁰ andR¹¹ is independently halogen, hydroxy, cyano, nitro, amino, C₁-C₈ alkyl,C₁-C₈ cyanoalkyl, C₁-C₈ cyanoalkoxy, C₁-C₈ haloalkyl, C₁-C₈hydroxyalkyl, C₁-C₈ nitroalkyl, C₂-C₈ alkenyl, C₂-C₈ haloalkenyl, C₂-C₈nitroalkenyl, C₂-C₈ alkynyl, C₂-C₈ haloalkynyl, C₂-C₈ alkoxyalkyl, C₃-C₈alkoxyalkoxyalkyl, C₂-C₈ haloalkoxyalkyl, C₂-C₈ haloalkoxyhaloalkoxy,C₃-C₆ cycloalkyl, cyclopropylmethyl, 1-methylcyclopropyl,2-methylcyclopropyl, C₄-C₁₀ cycloalkylalkyl, C₄-C₁₀ halocycloalkylalkyl,C₅-C₁₂ alkylcycloalkylalkyl, C₅-C₁₂ cycloalkylalkenyl, C₅-C₁₂cycloalkylalkynyl, C₃-C₈ cycloalkyl, C₃-C₈ halocycloalkyl, C₄-C₁₀alkylcycloalkyl, C₆-C₁₂ cycloalkylcycloalkyl, C₃-C₈ cycloalkenyl, C₃-C₈halocycloalkenyl, C₂-C₈ haloalkoxyalkoxy, C₂-C₈ alkoxyalkoxy, C₄-C₁₀cycloalkoxyalkyl, C₂-C₈ alkylthioalkyl, C₂-C₈ alkylsulfinylalkyl, C₂-C₈alkylsulfonylalkyl, C₂-C₈ alkylamino, C₂-C₈ dialkylamino, C₂-C₈halodialkylamino, C₂-C₈ alkylaminoalkyl, C₂-C₈ haloalkylaminoalkyl,C₄-C₁₀ cycloalkylaminoalkyl, C₃-C₁₀ dialkylaminoalkyl, —CHO, C₂-C₈alkylcarbonyl, C₂-C₈ haloalkylcarbonyl, C₄-C₁₀ cycloalkylcarbonyl,—C(═O)OH, C₂-C₈ alkoxycarbonyl, C₂-C₈ haloalkoxycarbonyl, C₄-C₁₀cycloalkoxycarbonyl, C₅-C₁₂ cycloalkylalkoxycarbonyl, —C(═O)NH₂, C₂-C₈alkylaminocarbonyl, C₄-C₁₀ cycloalkylaminocarbonyl, C₃-C₁₀dialkylaminocarbonyl, C₁-C₈ alkoxy, C₁-C₈ haloalkoxy, C₂-C₈ alkenyloxy,C₂-C₈ haloalkenyloxy, C₃-C₈ alkynyloxy, C₃-C₈ haloalkynyloxy, C₃-C₈cycloalkoxy, C₃-C₈ halocycloalkoxy, C₄-C₁₀ cycloalkylalkoxy, C₃-C₁₀alkylcarbonylalkoxy, C₂-C₈ alkylcarbonyloxy, C₂-C₈ haloalkylcarbonyloxy,C₄-C₁₀ cycloalkylcarbonyloxy, C₁-C₈ alkylsulfonyloxy, C₁-C₈haloalkylsulfonyloxy, C₁-C₈ alkylthio, C₁-C₈ haloalkylthio, C₃-C₈cycloalkylthio, C₁-C₈ alkylsulfinyl, C₁-C₈ haloalkylsulfinyl, C₁-C₈alkylsulfonyl, C₁-C₈ haloalkylsulfonyl, C₃-C₈ cycloalkylsulfonyl,formylamino, C₂-C₈ alkylcarbonylamino, C₂-C₈ haloalkylcarbonylamino,C₃-C₈ cycloalkylamino, C₂-C₈ alkoxycarbonylamino, C₁-C₆alkylsulfonylamino, C₁-C₆ haloalkylsulfonylamino, —SF₅, —SCN, SO₂NH₂,C₃-C₁₂ trialkylsilyl, C₄-C₁₂ trialkylsilylalkyl or C₄-C₁₂trialkylsilylalkoxy; or G²; or R²⁰S(═O)═N—, R²⁰S(═O)₂NR¹⁹—C(═O)— orR²⁰(R¹⁹N═)_(q)S(═O)_(p)—, wherein the free bond projecting to the rightindicates the connecting point to Q¹; or each R¹² and R¹³ isindependently cyano, C₁-C₃ alkyl, C₁-C₈ hydroxyalkyl, C₂-C₃ alkenyl,C₂-C₃ alkynyl, C₃-C₆ cycloalkyl, C₂-C₃ alkoxyalkyl, C₁-C₃ alkoxy, C₂-C₃alkylcarbonyl, C₂-C₃ alkoxycarbonyl, C₂-C₃ alkylaminoalkyl or C₃-C₄dialkylaminoalkyl; each R¹⁴ is independently H, cyano, C₂-C₃alkylcarbonyl or C₂-C₃ haloalkylcarbonyl; each R¹⁵ is independently H,cyano, hydroxy, CHO, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₁-C₄ alkoxy, C₂-C₆alkylcarbonyl, C₂-C₆ haloalkylcarbonyl, —(C═O)CH₃ or —(C═O)CF₃; each G¹is independently phenyl; or a 5- or 6-membered heterocyclic ring, eachsubstituted or unsubstituted on ring members with up to 5 substituentsindependently selected from R¹⁷; each W^(E), W^(F) and W^(G) isindependently —C(═O)—, —C(═O)O—, —C(═O)NH— or —S(═O)₂—; each G^(E),G^(F) and G^(G) is independently phenyl substituted or unsubstitutedwith R¹⁶; or a 5- or 6-membered heterocyclic ring, each heterocyclicring substituted or unsubstituted on ring members with up to 5substituents independently selected from R¹⁶; each G² is independentlyphenyl, phenylmethyl, pyridinylmethyl, phenylcarbonyl, phenoxy,phenylethynyl, phenylsulfonyl or a 5- or 6-membered heterocyclic ring,each substituted or unsubstituted on ring members with up to 5substituents independently selected from R¹⁸; each R¹⁶, R¹⁷ and R¹⁸ isindependently halogen, cyano, hydroxy, amino, nitro, —CHO, —C(═O)OH,—C(═O)NH₂, —SO₂NH₂, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₂-C₆ alkenyl, C₂-C₆alkynyl, C₂-C₈ alkylcarbonyl, C₂-C₈ haloalkylcarbonyl, C₂-C₈alkoxycarbonyl, C₄-C₁₀ cycloalkoxycarbonyl, C₅-C₁₂cycloalkylalkoxycarbonyl, C₂-C₈ alkylaminocarbonyl, C₃-C₁₀dialkylaminocarbonyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, C₂-C₈alkylcarbonyloxy, C₁-C₆ alkylthio, C₁-C₆ haloalkylthio, C₁-C₆alkylsulfinyl, C₁-C₆ haloalkylsulfinyl, C₁-C₆ alkylsulfonyl, C₁-C₆haloalkylsulfonyl, C₁-C₆ alkylaminosulfonyl, C₂-C₈ dialkylaminosulfonyl,C₃-C₁₀ trialkylsilyl, C₁-C₆ alkylamino, C₂-C₈ dialkylamino, C₂-C₈alkylcarbonylamino, C₁-C₆ alkylsulfonylamino, phenyl, pyridinyl orthienyl; each R¹⁹ is independently H, cyano, C₂-C₃ alkylcarbonyl orC₂-C₃ haloalkylcarbonyl; each R²⁰ is independently H, C₁-C₆ alkyl, C₃-C₈cycloalkyl, C₄-C₈ cycloalkylalkyl, C₁-C₆ haloalkyl, C₂-C₆ alkenyl, C₃-C₆alkynyl, C₂-C₈ alkoxyalkyl, C₂-C₈ haloalkoxyalkyl, C₂-C₈ alkylthioalkyl,C₂-C₈ alkylsulfinylalkyl, C₂-C₈ alkylsulfonylalkyl, C₁-C₆ alkoxy orC₃-C₁₀ trialkylsilyl; or G¹; each u and v are independently 0, 1 or 2 ineach instance of S(═O)_(u)(═NR¹⁴)_(v), provided that the sum of u and vis 0, 1 or 2; and each p and q are independently 0, 1 or 2 in eachinstance of R²⁰(R¹⁹N═)_(q)S(═O)_(p)—, provided that the sum of u and vis 0, 1 or 2 and when p is 0, q is other than 1 or
 2. 2. The compound ofclaim 1 wherein R^(A) is C₁-C₇ alkyl, C₁-C₇ haloalkyl, C₃-C₉ cycloalkyl,C₁-C₇ alkoxy or C₁-C₇ haloalkoxy, C₃-C₉ cycloalkoxy, each substituted orunsubstituted with up to 2 substituents independently selected from R⁸or G¹; or R^(A) is G¹; R^(B) is H, C₁-C₄ alkoxy, C₁-C₄ haloalkyl orC₁-C₄ alkyl; R^(C) is H, C₁-C₄ alkoxy, C₁-C₄ haloalkyl or C₁-C₄ alkyl;R^(D) is H, C₁-C₃ alkyl or C₂-C₃ alkylcarbonyl; R^(E) is H, hydroxy,amino, cyano, formyl, —C(O)NH₂, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₂-C₆cyanoalkyl, C₃-C₆ cycloalkyl, C₄-C₈ cycloalkylalkyl, C₂-C₈ alkoxyalkyl,C₃-C₈ alkoxyalkoxyalkyl, C₂-C₈ haloalkoxyalkyl, C₂-C₈ alkenyl, C₂-C₈haloalkenyl, C₂-C₈ alkenylalkyl, C₂-C₈ haloalkenylalkyl, C₂-C₈alkylcarbonyl, C₂-C₈ haloalkylcarbonyl, C₄-C₁₀ cycloalkylcarbonyl,C₅-C₁₀ cycloalkylcarbonylalkyl, C₂-C₈ alkoxycarbonyl, C₂-C₈haloalkoxycarbonyl, C₄-C₁₀ cycloalkoxycarbonyl, C₂-C₈alkylaminocarbonyl, C₃-C₁₀ dialkylaminocarbonyl, C₄-C₁₀cycloalkylaminocarbonyl, C₁-C₆ alkoxy, C₁-C₆ alkylsulfinyl, C₁-C₆haloalkylsulfinyl, C₃-C₈ cycloalkylsulfinyl, C₁-C₆ alkylsulfonyl, C₁-C₆haloalkylsulfonyl, C₃-C₈ cycloalkylsulfonyl, C₁-C₆ alkylaminosulfonyl orC₂-C₈ dialkylaminosulfonyl; R^(F) is formyl, —C(O)NH₂, C₂-C₈alkylcarbonyl, C₂-C₈ haloalkylcarbonyl, C₄-C₁₀ cycloalkylcarbonyl, C₂-C₈alkoxycarbonyl, C₂-C₈ haloalkoxycarbonyl, C₄-C₁₀ cycloalkoxycarbonyl,C₂-C₈ alkylaminocarbonyl, C₃-C₁₀ dialkylaminocarbonyl, C₄-C₁₀cycloalkylaminocarbonyl, C₁-C₆ alkylsulfinyl, C₁-C₆ haloalkylsulfinyl,C₃-C₈ cycloalkylsulfinyl, C₁-C₆ alkylsulfonyl, C₁-C₆ haloalkylsulfonyl,C₃-C₈ cycloalkylsulfonyl, C₁-C₆ alkylaminosulfonyl, C₂-C₈dialkylaminosulfonyl, —P(═O)(OH)₂, C₁-C₆ dialkylphosphoryl, C₁-C₆haloalkylphosphoryl, C₃-C₈ cycloalkylphosphoryl, C₂-C₈dialkoxyphosphoryl, C₆-C₁₄ dicycloalkoxyphosphoryl, C₈-C₁₆dicycloalkylalkoxyphosphoryl, C₂-C₁₂ bis(alkylamino)phosphoryl, C₄-C₂₄bis(dialkylamino)phosphoryl; or phenyl substituted or unsubstituted withR¹⁶; R^(G) is formyl, —C(O)NH₂, C₂-C₈ alkylcarbonyl, C₂-C₈haloalkylcarbonyl, C₄-C₁₀ cycloalkylcarbonyl, C₂-C₈ alkoxycarbonyl,C₂-C₈ haloalkoxycarbonyl, C₄-C₁₀ cycloalkoxycarbonyl, C₂-C₈alkylaminocarbonyl, C₃-C₁₀ dialkylaminocarbonyl, C₄-C₁₀cycloalkylaminocarbonyl, C₁-C₆ alkylsulfinyl, C₁-C₆ haloalkylsulfinyl,C₃-C₈ cycloalkylsulfinyl, C₁-C₆ alkylsulfonyl, C₁-C₆ haloalkylsulfonyl,C₃-C₈ cycloalkylsulfonyl or C₁-C₆ alkylaminosulfonyl; Q¹ is a phenylring or a naphthalenyl ring system, each ring or ring system substitutedor unsubstituted with up to 5 substituents independently selected fromR¹⁰; or a 5- to 6-membered heterocyclic ring; or an 8- to 10-memberedbicyclic ring system, each ring or ring system containing ring membersselected from carbon atoms and 1 to 4 heteroatoms independently selectedfrom up to 2 O, up to 2 S and up to 4 N atoms, wherein up to 2 carbonring members are independently selected from C(═O) and C(═S), and thesulfur atom ring members are independently selected fromS(═O)_(u)(═NR¹⁴)_(v), each ring or ring system substituted orunsubstituted with up to 4 substituents independently selected from R¹⁰on carbon atom ring members and selected from R¹² on nitrogen atom ringmembers; Q² is a phenyl ring, each ring substituted or unsubstitutedwith up to 4 substituents independently selected from R¹¹; or a 5- to6-membered heterocyclic ring; or an 8- to 10-membered bicyclic ringsystem, each ring or ring system containing ring members selected fromcarbon atoms and 1 to 4 heteroatoms independently selected from up to 2O, up to 2 S and up to 4 N atoms, wherein up to 2 carbon ring membersare independently selected from C(═O) and C(═S), and the sulfur atomring members are independently selected from S(═O)_(u)(═NR¹⁴)_(v), eachring or ring system substituted or unsubstituted with up to 4substituents independently selected from R¹¹ on carbon atom ring membersand selected from R¹³ on nitrogen atom ring members; J is —CR²R³—,—CR²R³—CR⁴R⁵— or —NR⁶—; Y¹ and Y² are each independently O or S; R¹ isH, CHO, C₃-C₈ alkylcarbonylalkyl, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₂-C₆alkenyl, C₃-C₆ alkynyl, C₂-C₆ cyanoalkyl, C₃-C₆ cycloalkyl, C₄-C₈cycloalkylalkyl, C₂-C₈ alkoxyalkyl, C₃-C₈ alkoxyalkoxyalkyl, C₂-C₈haloalkoxyalkyl, C₂-C₈ alkylthioalkyl, C₂-C₈ alkylcarbonyl, C₂-C₈haloalkylcarbonyl, C₄-C₁₀ cycloalkylcarbonyl, C₂-C₈ alkoxycarbonyl,C₂-C₈ haloalkoxycarbonyl, C₂-C₈ alkylaminocarbonyl, C₃-C₁₀dialkylaminocarbonyl or C₄-C₁₀ cycloalkylaminocarbonyl; R² and R³ areeach independently H or C₁-C₄ alkyl; R⁴ and R⁵ are each independently H,halogen, C₁-C₄ alkyl or C₁-C₄ alkoxy; R⁶ is H, C₁-C₆ alkyl or C₁-C₆alkoxy; R⁷ is H, halogen, C₁-C₄ alkoxy or C₁-C₄ alkyl; each R⁸ isindependently cyano, nitro, —CHO, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₂-C₈alkylcarbonyl, C₂-C₈ haloalkylcarbonyl, C₂-C₈ alkoxycarbonyl, C₄-C₁₀cycloalkoxycarbonyl, C₅-C₁₂ cycloalkylalkoxycarbonyl, C₂-C₈alkylaminocarbonyl, C₃-C₁₀ dialkylaminocarbonyl, C₁-C₆ alkoxy, C₁-C₆haloalkoxy or C₂-C₈ alkylcarbonyloxy; R⁹ is H, C₁-C₆ alkyl, C₂-C₈alkoxyalkyl, C₂-C₈ alkylthioalkyl, C₂-C₈ alkylsulfinylalkyl, C₂-C₈alkylsulfonylalkyl, C₂-C₈ alkylcarbonyl, C₄-C₁₀ cycloalkylcarbonyl,C₂-C₈ alkoxycarbonyl or C₄-C₁₀ cycloalkoxycarbonyl; each R¹⁰ and R¹¹ ishalogen, nitro, C₁-C₈ alkyl, C₁-C₈ cyanoalkyl, C₁-C₈ cyanoalkoxy, C₁-C₈haloalkyl, C₁-C₈ nitroalkyl, C₂-C₈ alkenyl, C₂-C₈ haloalkenyl, C₂-C₈nitroalkenyl, C₂-C₈ alkoxyalkyl, C₃-C₈ alkoxyalkoxyalkyl, C₂-C₈haloalkoxyalkyl, C₂-C₈ haloalkoxyhaloalkoxy, C₄-C₁₀ cycloalkylalkyl,C₄-C₁₀ halocycloalkylalkyl, C₅-C₁₂ alkylcycloalkylalkyl, C₅-C₁₂cycloalkylalkenyl, C₃-C₈ cycloalkyl, C₃-C₈ halocycloalkyl, C₄-C₁₀alkylcycloalkyl, C₆-C₁₂ cycloalkylcycloalkyl, C₃-C₈ cycloalkenyl, C₃-C₈halocycloalkenyl, C₂-C₈ haloalkoxyalkoxy, C₂-C₈ alkoxyalkoxy, C₄-C₁₀cycloalkoxyalkyl, C₂-C₈ alkylcarbonyl, C₂-C₈ haloalkylcarbonyl, C₄-C₁₀cycloalkylcarbonyl, —C(═O)OH, C₂-C₈ alkoxycarbonyl, C₂-C₈haloalkoxycarbonyl, C₄-C₁₀ cycloalkoxycarbonyl, C₅-C₁₂cycloalkylalkoxycarbonyl, —C(═O)NH₂, C₁-C₈ alkoxy, C₁-C₈ haloalkoxy,C₂-C₈ alkenyloxy, C₂-C₈ haloalkenyloxy, C₃-C₈ cycloalkoxy, C₃-C₈halocycloalkoxy, C₄-C₁₀ cycloalkylalkoxy, C₃-C₁₀ alkylcarbonylalkoxy,C₂-C₈ alkylcarbonyloxy, C₂-C₈ haloalkylcarbonyloxy, C₄-C₁₀cycloalkylcarbonyloxy, C₁-C₈ alkylsulfonyloxy, C₁-C₈haloalkylsulfonyloxy, C₁-C₈ alkylsulfonyl, C₁-C₈ haloalkylsulfonyl,C₃-C₈ cycloalkylsulfonyl; each G¹ is independently phenyl; or a6-membered heterocyclic ring, each substituted or unsubstituted on ringmembers with up to 4 substituents independently selected from R¹⁷; eachR¹⁶ and R¹⁷ is independently halogen, cyano, hydroxy, amino, nitro,—CHO, —C(═O)OH, —C(═O)NH₂, —SO₂NH₂, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₂-C₆alkenyl, C₂-C₆ alkynyl, C₂-C₈ alkylcarbonyl, C₁-C₈ hydroxyalkyl, C₂-C₈haloalkylcarbonyl, C₂-C₆ alkoxyalkyl, C₂-C₆ alkylaminoalkyl, C₂-C₈alkoxycarbonyl, C₃-C₈ cycloalkyl, C₄-C₁₀ cycloalkoxycarbonyl, C₅-C₁₂cycloalkylalkoxycarbonyl, C₂-C₈ alkylaminocarbonyl, C₃-C₁₀dialkylaminocarbonyl, C₃-C₈ dialkylaminoalkyl, C₁-C₆ alkoxy, C₁-C₆haloalkoxy, C₂-C₈ alkylcarbonyloxy or C₁-C₆ alkylthio; and provided thesum of u and v is
 2. 3. The compound of claim 2 wherein L is selectedfrom L-1, L-2 or L-3; R^(A) is C₁-C₇ alkyl, C₁-C₇ haloalkyl, C₁-C₇alkoxy or C₁-C₇ haloalkoxy; each substituted or unsubstituted with up to2 substituents independently selected from R⁸; or R^(A) is G¹; R^(B) isH, —OCH₃, CF₃ or CH₃; R^(C) is H, C₁-C₂ alkoxy or C₁-C₂ alkyl; R^(D) isH, CH₃, CH₂CH₃ or —C(═O)CH₃ CH₂CH₃; R^(E) is H, hydroxy, amino, cyano,formyl, —C(O)NH₂, C₁-C₆ alkyl, C₃-C₆ cycloalkyl, C₄-C₈ cycloalkylalkyl,C₂-C₈ alkoxyalkyl, C₃-C₈ alkoxyalkoxyalkyl, C₂-C₈ alkylcarbonyl, C₄-C₁₀cycloalkylcarbonyl, C₅-C₁₀ cycloalkylcarbonylalkyl, C₂-C₈alkoxycarbonyl, C₄-C₁₀ cycloalkoxycarbonyl, C₁-C₆ alkylsulfonyl; R^(F)is C₂-C₈ alkylcarbonyl, C₄-C₁₀ cycloalkylcarbonyl, C₂-C₈ alkoxycarbonyl,C₂-C₈ haloalkoxycarbonyl, C₄-C₁₀ cycloalkoxycarbonyl, C₂-C₈alkylaminocarbonyl, C₃-C₁₀ dialkylaminocarbonyl, C₄-C₁₀cycloalkylaminocarbonyl, C₁-C₆ alkylsulfonyl, C₁-C₆ haloalkylsulfonyl,C₃-C₈ cycloalkylsulfonyl or C₁-C₆ alkylaminosulfonyl; or phenylsubstituted or unsubstituted with R¹⁶; R^(G) is formyl, C₂-C₈alkylcarbonyl, C₂-C₈ alkoxycarbonyl, C₄-C₁₀ cycloalkoxycarbonyl, C₂-C₈alkylaminocarbonyl, C₄-C₁₀ cycloalkylaminocarbonyl, C₁-C₆ alkylsulfonyl,C₁-C₆ haloalkylsulfonyl, C₃-C₈ cycloalkylsulfonyl or C₁-C₆alkylaminosulfonyl; each R⁸ is independently C₂-C₆ alkenyl, C₁-C₆ alkoxyor C₁-C₆ haloalkoxy; J is —CR²R³— or —CR²R³—CR⁴R⁵—; Y¹ and Y² are eachindependently O; R¹ is H, C₃-C₈ alkylcarbonylalkyl, C₁-C₆ alkyl, C₁-C₆haloalkyl, C₂-C₆ cyanoalkyl, C₃-C₆ cycloalkyl, C₄-C₈ cycloalkylalkyl,C₂-C₈ alkoxyalkyl, C₂-C₈ haloalkoxyalkyl, C₂-C₈ alkylcarbonyl, C₂-C₈haloalkylcarbonyl, C₄-C₁₀ cycloalkylcarbonyl, C₂-C₈ alkoxycarbonyl orC₂-C₈ haloalkoxycarbonyl; Q¹ is a phenyl ring substituted orunsubstituted with up to 4 substituents independently selected from R¹⁰;or a 5- to 6-membered heterocyclic ring, each ring containing ringmembers selected from carbon atoms and 1 to 4 heteroatoms independentlyselected from up to 2 O, up to 2 S and up to 4 N atoms, each ringsubstituted or unsubstituted with up to 4 substituents independentlyselected from R¹⁰ on carbon atom ring members and selected from R¹² onnitrogen atom ring members; Q² is a phenyl ring, substituted orunsubstituted with up to 4 substituents independently selected from R¹¹;or a 5- to 6-membered heterocyclic ring; or an 8- to 10-memberedbicyclic ring system, each ring or ring system containing ring membersselected from carbon atoms and 1 to 4 heteroatoms independently selectedfrom up to 2 O, up to 2 S and up to 4 N atoms, wherein up to 2 carbonring members are independently selected from C(═O) and C(═S), and thesulfur atom ring members are independently selected fromS(═O)_(u)(═NR¹⁴)_(v), each ring or ring system substituted orunsubstituted with up to 4 substituents independently selected from R¹¹on carbon atom ring members and selected from R¹³ on nitrogen atom ringmembers; R² and R³ are each independently H or CH₃; R⁴ and R⁵ are eachindependently H, halogen or C₁-C₄ alkyl; R⁷ is H, F, Cl or CH₃; R⁹ is H,C₁-C₆ alkyl, C₂-C₈ alkoxyalkyl, C₂-C₈ alkylcarbonyl or C₂-C₈alkoxycarbonyl; each R¹⁰ and R¹¹ is independently halogen, C₁-C₈ alkyl,C₁-C₈ haloalkyl, C₂-C₈ alkoxyalkyl, C₃-C₈ alkoxyalkoxyalkyl, C₄-C₁₀cycloalkylalkyl, C₅-C₁₂ alkylcycloalkylalkyl, C₃-C₈ cycloalkyl, C₃-C₈halocycloalkyl, C₆-C₁₂ cycloalkylcycloalkyl, C₃-C₈ halocycloalkenyl,C₂-C₈ haloalkoxyalkoxy, C₂-C₈ alkoxyalkoxy, C₄-C₁₀ cycloalkoxyalkyl,C₂-C₈ alkylcarbonyl, C₂-C₈ haloalkylcarbonyl, C₄-C₁₀ cycloalkylcarbonyl,C₂-C₈ alkoxycarbonyl, C₄-C₁₀ cycloalkoxycarbonyl, C₅-C₁₂cycloalkylalkoxycarbonyl, C₁-C₈ alkoxy, C₁-C₈ haloalkoxy, C₂-C₈haloalkenyloxy, C₃-C₈ cycloalkoxy, C₃-C₈ halocycloalkoxy, C₄-C₁₀cycloalkylalkoxy, C₃-C₁₀ alkylcarbonylalkoxy or C₂-C₈haloalkylcarbonyloxy; each R¹² and R¹³ is independently C₁-C₃ alkyl,C₃-C₆ cycloalkyl or C₂-C₃ alkylcarbonyl; each R¹⁴ is independently H;R¹⁵ is H, CH₃, —(C═O)CH₃ or —(C═O)CF₃; each G¹ is independently phenylsubstituted or unsubstituted on ring members with up to 3 substituentsindependently selected from R¹⁷; and each R¹⁶ and R¹⁷ is independentlyhalogen, cyano, hydroxy, amino, nitro, —CHO, —C(═O)OH, —C(═O)NH₂,—SO₂NH₂, C₁-C₆ alkyl or C₁-C₆ haloalkyl.
 4. The compound of claim 3wherein L is selected from L-1 or L-2; R^(A) is C₁-C₇ alkyl or C₁-C₇alkoxy; each substituted or unsubstituted with up to 2 substituentsindependently selected from R⁸; R^(B) is H, —OCH₃ or CH₃; R^(C) is H orCH₃; R^(D) is CH₃ or CH₂CH₃; R^(E) is H, C₁-C₆ alkyl, C₃-C₆ cycloalkyl,C₄-C₈ cycloalkylalkyl, C₂-C₈ alkoxyalkyl, C₂-C₈ alkylcarbonyl, C₂-C₈alkoxycarbonyl, C₄-C₁₀ cycloalkoxycarbonyl, C₁-C₆ alkylsulfonyl; each R⁸is independently C₁-C₆ alkoxy or C₁-C₆ haloalkoxy; J is —CR²R³—; Y¹ andY² are each independently O; R¹ is H, C₁-C₆ alkyl, C₁-C₆ haloalkyl,C₂-C₆ cyanoalkyl, C₃-C₆ cycloalkyl, C₄-C₈ cycloalkylalkyl, C₂-C₈alkoxyalkyl, C₂-C₈ haloalkoxyalkyl or C₂-C₈ alkoxycarbonyl; Q¹ is aphenyl ring substituted or unsubstituted with up to 4 substituentsindependently selected from R¹⁰; Q² is a phenyl ring, substituted orunsubstituted with up to 4 substituents independently selected from R¹¹;or a 5- to 6-membered heterocyclic ring containing ring members selectedfrom carbon atoms and 1 to 4 heteroatoms independently selected from upto 4 N atoms, wherein up to 2 carbon ring members are independentlyselected from C(═O) and C(═S), each ring or ring system substituted orunsubstituted with up to 4 substituents independently selected from R¹¹on carbon atom ring members and selected from R¹³ on nitrogen atom ringmembers; R² and R³ are each independently H; R⁷ is H or CH₃; R⁹ is H,C₁-C₆ alkyl or C₂-C₈ alkoxycarbonyl; each R¹⁰ and R¹¹ is independentlyhalogen, C₁-C₈ alkyl, C₁-C₈ haloalkyl, C₂-C₈ alkoxyalkyl, C₄-C₁₀cycloalkylalkyl, C₅-C₁₂ alkylcycloalkylalkyl, C₃-C₈ cycloalkyl, C₃-C₈halocycloalkyl, C₂-C₈ haloalkoxyalkoxy, C₁-C₈ alkoxy, C₁-C₈ haloalkoxyor C₂-C₈ alkoxyalkoxy; and each R¹² and R¹³ is independently C₁-C₃ alkylor C₂-C₃ alkylcarbonyl.
 5. The compound of claim 4 wherein L is selectedfrom L-1; R^(A) is C₁-C₃ alkyl substituted or unsubstituted with up to 2substituents independently selected from R⁸; each R⁸ is independentlyC₁-C₆ alkoxy; R¹ is H, C₁-C₆ alkyl, C₃-C₆ cycloalkyl, C₄-C₈cycloalkylalkyl or C₂-C₈ alkoxyalkyl; Q¹ is a phenyl ring substituted orunsubstituted with up to 3 substituents independently selected from R¹⁰;Q² is a phenyl ring, substituted or unsubstituted with up to 4substituents independently selected from R¹¹; R⁷ is H; R⁹ is H, CH₃ or—C(═O)CH₃; and each R¹⁰ and R¹¹ is independently halogen, C₁-C₈ alkyl,C₁-C₈ haloalkyl, C₃-C₈ cycloalkyl, C₁-C₈ alkoxy or C₁-C₈ haloalkoxy. 6.The compound of claim 4 wherein L is selected from L-1; R^(A) is C₁-C₃alkoxy, substituted or unsubstituted with up to 2 substituentsindependently selected from R⁸; each R⁸ is independently C₁-C₆ alkoxy;R¹ is H, CH₃, CH₂CH₃, cyclopropyl, cyclopropylmethyl or CH₂OCH₃; Q¹ is aphenyl ring substituted or unsubstituted with up to 2 substituentsindependently selected from R¹⁰; Q² is a phenyl ring, substituted orunsubstituted with up to 3 substituents independently selected from R¹¹;R⁷ is H; R⁹ is H; and each R¹⁰ and R¹¹ is independently halogen, C₁-C₈alkyl, C₁-C₈ haloalkyl, C₁-C₈ alkoxy or C₁-C₈ haloalkoxy.
 7. A compoundof claim 1 selected from the group consisting of(3S,4R)—N-(2,3-difluorophenyl)-3-(hydroxymethyl)-1-methyl-2-oxo-4-[4-(trifluoromethyl)-3-pyrrolidinecarboxamide(cis);(3R,4S)—N-(2,3-difluorophenyl)-3-(hydroxymethyl)-1-methyl-2-oxo-4-[4-(trifluoromethyl)-3-pyrrolidinecarboxamide(trans);(3S,4R)-3-[(acetyloxy)methyl]-N-(2,3-difluorophenyl)-1-methyl-2-oxo-4-[4-(trifluoromethyl)-3-pyrrolidinenecarboxamide;and(3S,4R)-3-acetyl-N-(2,3-difluorophenyl)-1-methyl-2-oxo-4-[4-(trifluoromethyl)-3-pyrrolidinecarboxamide.8. A herbicidal composition comprising a compound of claim 1 and atleast one component selected from the group consisting of surfactants,solid diluents and liquid diluents.
 9. A herbicidal compositioncomprising a compound of claim 1, at least one additional activeingredient selected from the group consisting of other herbicides andherbicide safeners, and at least one component selected from the groupconsisting of surfactants, solid diluents and liquid diluents.
 10. Aherbicidal mixture comprising (a) a compound of claim 1, and (b) atleast one additional active ingredient selected from (b1) photosystem IIinhibitors, (b2) acetohydroxy acid synthase (AHAS) inhibitors, (b3)acetyl-CoA carboxylase (ACCase) inhibitors, (b4) auxin mimics, (b5)5-enol-pyruvylshikimate-3-phosphate (EPSP) synthase inhibitors, (b6)photosystem I electron diverters, (b7) protoporphyrinogen oxidase (PPO)inhibitors, (b8) glutamine synthetase (GS) inhibitors, (b9) very longchain fatty acid (VLCFA) elongase inhibitors, (b10) auxin transportinhibitors, (b11) phytoene desaturase (PDS) inhibitors, (b12)4-hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitors, (b13)homogentisate solenesyltransererase (HST) inhibitors, (b14) cellulosebiosynthesis inhibitors, (b15) other herbicides including mitoticdisruptors, organic arsenicals, asulam, bromobutide, cinmethylin,cumyluron, dazomet, difenzoquat, dymron, etobenzanid, flurenol,fosamine, fosamine-ammonium, hydantocidin, metam, methyldymron, oleicacid, oxaziclomefone, pelargonic acid and pyributicarb, and (b16)herbicide safeners; and salts of compounds of (b1) through (b16).
 11. Amethod for controlling the growth of undesired vegetation comprisingcontacting the vegetation or its environment with a herbicidallyeffective amount of a compound of claim 1.